10.1002/ejoc.201900974
European Journal of Organic Chemistry
FULL PAPER
124.1, 124.0, 87.9, 84.2, 83.0, 41.0, 40.2, 35.9, 35.5, 32.0,
30.1, 29.8, 29.7, 26.2, 26.0, 22.7, 22.7, 14.1, 14.1.
38.1%). Rf= 0.7 (15% ethyl acetate in petroleum ether). IR
(Neat Film, KBr) IR 2925.10, 2851.80, 1680.99, 1614.45,
1449.53, 1124.52, 1060.87, 814.94, 755.14 1H NMR (400 MHz,
CDCl3) δ 7.60 (dd, J = 13.3, 7.7 Hz, 1H), 7.43– 7.25 (m, 5H
including CDCl3), 6.09 (d, J = 9.8 Hz, 1H), 4.18-4.13 (m, 1H),
2.50-2.47 (m, 1H), 2.22-2.18 (m, 1H), 2.01-1.70 (m, 6H), 1.41-
1.02 (m, 6H); 13C NMR (100 MHz, CDCl3) δ 203.0, 146.5,
144.1, 130.3, 129.6, 128.9, 128.8, 127.6, 125.5, 124.1, 88.9,
87.8, 42.8, 41.0, 30.9, 29.1, 27.9, 26.6, 26.0, 25.8; HRMS
(ESI) calc’d for C19H22NaO2 [M+Na]+ : 305.1512, Found:
305.1510.
(1'S, 5R)-5-cyclohexyl-4, 5-dihydro-2'H, 3H-spiro [furan-2,
1'-naphthalen]-2'-one (j2). Elution with 2% ethyl acetate in
petroleum ether afforded yellow liquid (10.5 mg, 0.037 mmol,
61.9%). Rf= 0.7 (15% ethyl acetate in petroleum ether). IR
(Neat Film, KBr) IR 2923.17, 2850.84, 1683.89, 1448.57,
1057.01, 820.77, 755.141H NMR (400 MHz, CDCl3) δ 7.64 (d, J
= 7.7 Hz, 1H), 7.43-7.27(m, 5H including CDCl3), 6.10 (d, J =
9.9 Hz, 1H), 4.32 (dd, J = 13.9, 7.4 Hz 1H), 2.43-2.38 (m, 1H),
2.15 – 2.09 (m, 2H), 1.89 – 1.65 (m, 6H), 1.35 – 1.13 (m, 6H);
13C NMR (100 MHz, CDCl3) δ 204.5, 145.6, 144.5, 130.1,
129.6, 129.1, 127.7, 125.4, 124.1, 87.2, 86.6, 43.1, 40.2, 30.0,
29.3, 27.8, 26.6, 26.1, 26.0; HRMS (ESI) calc’d for C19H22NaO2
[M+Na]+ : 305.1512, Found: 305.1511.
(1'S, 5R)-5-pentyl-4, 5-dihydro-2'H, 3H-spiro[furan-2,1'-
naphthalen]-2'-one (e1). Elution with 1% ethyl acetate in
petroleum ether afforded yellow liquid (4 mg, 0.015 mmol,
26.7%). Rf= 0.7 (15% ethyl acetate in petroleum ether). IR
1
(Neat Film, KBr) 2955.00, 1680.03, 1056.04, 755.14; H NMR
(400 MHz, CDCl3) δ 7.60 (d, J = 7.5 Hz, 1H), 7.41 (td, J = 7.4,
1.8 Hz, 1H), 7.34 (d, J = 9.9 Hz, 1H), 7.32 – 7.25 (m, 2H), 6.10
(d, J = 9.9 Hz, 1H), 4.52-4.48 (m, 1H), 2.52-2.47 (m, 1H), 2.09
– 1.75 (m, 4H), 1.55 – 1.27 (m, 4H), 0.98-0.90 (m, 3H); 13C
NMR (101 MHz, CDCl3) δ 202.8, 146.3, 144.0, 130.2, 129.7,
128.9, 127.6, 125.5, 124.1, 88.2, 84.1, 41.0, 35.5, 32.0, 29.9,
26.1, 22.6, 14.0; HRMS (ESI) calc’d for C18H22NaO2 [M+Na]+ :
2993.1512, Found: 293.1511.
(1'S, 5S)-5-pentyl-4, 5-dihydro-2'H, 3H-spiro[furan-2, 1'-
naphthalen]-2'-one (e2). Elution with 2% ethyl acetate in
petroleum ether afforded yellow liquid (11 mg, 0.04 mmol,
73.3%). Rf= 0.7 (15% ethyl acetate in petroleum ether). IR
(Neat Film, KBr) 2857.59,1684.03, 1060.87, 755.14; 1H NMR
(400 MHz, CDCl3) δ 7.62 (d, J = 7.8 Hz, 1H), 7.43 – 7.27 (m,
4H), 6.11 (d, J = 9.9 Hz, 1H), 4.61 – 4.54 (m, 1H), 2.43-2.40 (m,
1H), 2.22 – 2.17 (m, 1H), 1.95 – 1.88 (m, 2H), 1.74 – 1.66 (m,
3H), 1.42-1.37(m, 3H), 0.97-0.90 (m, 3H); 13C NMR (100 MHz,
CDCl3) δ 204.0, 145.5, 144.6, 130.1, 129.6, 129.1, 127.7,
125.4, 124.0, 87.6, 83.0, 40.2, 35.9, 32.0, 30.1, 26.0, 22.7,
14.1; HRMS (ESI) calc’d for C18H22NaO2 [M+Na]+ : 2993.1512,
Found: 293.1514.
5-octyl-4, 5-dihydro-2'H, 3H-spiro[furan-2,1'-naphthalen]-2'-
one (l). Was synthesized according to the general procedure B
with 1-(3-hydroxyundecyl)naphthalen-2-ol (20 mg, 0.063 mmol)
and TBATB salt using THF as a solvent at room temperature
(30°C). Total reaction time was 24 hrs. The product was
obtained as a yellow liquid (15 mg, 0.048 mmol, 75%) after
elution with 10% ethyl ace-tate in petroleum ether of the crude
reaction mixture. (Rf= 0.8, 15% ethyl acetate in petroleum
ether) 1H NMR (400 MHz, CDCl3) for the diastereomeric
mixture (l2:l1 = 2.6:1) δ 7.60 (t, J = 7.8 Hz, 1H), 7.42 – 7.24 (m,
2H), 6.10 (d, J = 9.9 Hz, 1H), 4.61 – 4.54 (m, 1H), 4.53-4.46 (m,
1H), 2.51-2.47 (m, 1H), 2.44 – 2.37 (m, 1H), 2.23 – 2.15 (m,
1H), 2.08-2.01 (m, 1H), 1.96 – 1.82 (m, 2H), 1.74 – 1.63 (m,
2H), 1.59 – 1.51 (m, 1H), 1.48 – 1.41 (m, 1H), 1.39-1.21 (m,
6H), 0.92-0.84 (m, 3H); 13C NMR (100 MHz, CDCl3) δ 204.3,
203.0, 146.3, 145.5, 144.6, 144.2, 130.3, 130.1, 129.6, 129.6,
129.1, 128.9, 127.7, 127.6, 125.5, 125.4, 124.1, 124.0, 88.2,
87.9, 84.2, 83.0, 63.1, 41.0, 40.2, 35.9, 35.5, 31.9, 31.8, 30.1,
29.8, 29.7, 29.6, 29.6, 29.3, 29.3, 26.5, 26.3, 22.7, 14.2.
5-(p-tolyl)-4,
5-dihydro-2'H,
3H-spiro[furan-2,1'-
naphthalen]-2'-one (m). Was synthesized according to the
general procedure B with 1-(3-hydroxyundecyl)naphthalen-2-ol
(20 mg, 0.068 mmol) and TBATB salt using THF as a solvent
at room temperature (30°C). Total reaction time was 11 hrs.
The product was obtained as a yellow liquid (18 mg, 0.062
mmol, 93%) after elution with 10% ethyl acetate in petroleum
ether of the crude reaction mixture. (Rf = 0.5, 15% ethyl
1
acetate in petroleum ether) H NMR (400 MHz, CDCl3) δ 7.76
(d, J = 8.0 Hz, 1H), 7.71 (t, J = 7.3 Hz, 1H), 7.48 – 7.38 (m,
3H), 7.34 – 7.24 (m, 4H), 6.16 (dd, J = 9.9, 2.5 Hz, 1H), 5.64 (t,
J = 7.0 Hz, 1H), 5.56 – 5.36 (m, 1H), 2.70-2.65 (m 1H), 2.61 –
2.52 (m, 1H), 2.40 (d, J = 6.6 Hz, 4H), 2.33 – 2.29 (m, 1H),
2.16 – 2.06 (m, 1H); 13C NMR (101 MHz, CDCl3) δ 202.72,
146.24, 144.92, 144.39, 138.48, 137.50, 130.43, 130.27,
129.64, 129.27, 129.20, 129.08, 127.92, 127.83, 126.95,
126.95, 126.07, 125.76, 125.61, 124.08, 124.02, 88.09, 85.66,
83.61, 41.52, 40.75, 33.50, 32.81, 21.29, 21.24.
(1'S, 5S)-5-(p-tolyl)-4, 5-dihydro-2'H, 3H-spiro [furan-2, 1'-
naphthalen]-2'-one. (m1) Elution with 3% ethyl acetate in
petroleum ether afforded yellow liquid (4.6 mg, 0.016 mmol,
25.7%). Rf= 0.5 (15% ethyl acetate in petroleum ether). IR
(Neat Film, KBr) 2973.26, 1683.91, 1650.02, 756.13 cm-1; 1H
NMR (400 MHz, CDCl3) δ 7.76 – 7.65 (m, 3H), 7.46- 7.36 (m,
2H), 7.32 – 7.19 (m, 4H), 6.15 (d, J = 10.0 Hz, 1H), 5.45 (dd, J
= 14.8, 8.4 Hz, 1H), 2.70-2.62(m, 1H), 2.40- 2.25(m, 5H), 2.14-
2.06(m, 1H); 13C NMR (100 MHz, CDCl3) δ 202.38, 144.32,
130.39, 129.05, 127.80, 126.92, 125.61, 124.10, 85.64, 77.19,
41.50, 33.47, 21.24; HRMS (ESI) calc’d for C20H18O2Na
[M+Na]+: 313.1199, Found : 313.1193.
(1'S, 5R)-5-(p-tolyl)-4, 5-dihydro-2'H, 3H-spiro [furan-2, 1'-
naphthalen]-2'-one. (m2) Elution with 4% ethyl acetate in
petroleum ether afforded yellow liquid (13.4 mg, 0.046 mmol,
74.3%). Rf= 0.5 (15% ethyl acetate in petroleum ether). IR
(Neat Film, KBr) 2989.36, 1681.35, 1660.61, 755.14 cm-1; 1H
NMR (400 MHz, CDCl3) δ 7.71 (d, J = 7.6 Hz, 1H), 7.46 (d, J =
8.0 Hz, 2H), 7.43 – 7.38 (m, 2H), 7.33 (dd, J = 4.2, 1.9 Hz, 2H),
7.29 – 7.24 (m, 2H), 6.16 (d, J = 9.9 Hz, 1H), 5.63 (t, J = 7.0
Hz, 1H), 2.60 – 2.51 (m, 2H), 2.41 (s, 3H), 2.16-2.06 (m, 2H);
13C NMR (100 MHz, CDCl3) δ 204.06, 145.12, 144.88, 138.73,
137.22, 130.25, 129.54, 129.24, 129.18, 129.06, 127.90,
126.93, 126.06, 125.77, 124.02, 87.63, 83.60, 40.72, 32.79,
21.21; HRMS (ESI) calc’d for C20H18O2Na [M+Na]+ : 313.1199,
Found : 313.1196.
5-cyclohexyl-4,
naphthalen]-2'-one (j). Was synthesized according to the
general procedure with 1-(3-cyclohexyl-3-
5-dihydro-2'H,
3H-spiro[furan-2,1'-
B
hydroxypropyl)naphthalen-2-ol (20 mg, 0.07 mmol) and TBATB
salt using THF as a solvent at room temperature (30°C). Total
reaction time was 19 hrs. The product was obtained as a
yellow liquid (17 mg, 0.06 mmol, 83%) after elution with 10%
ethyl ace-tate in petroleum ether of the crude reaction mixture.
(Rf= 0.7, 15% ethyl acetate in petroleum ether) 1H NMR (400
MHz, CDCl3) for the diastereomeric mixture (j2:j1 = 1.6:1) δ
7.63 (d, J = 7.6 Hz, 1H), 7.58(d, J=7.7 Hz, 1H), 7.42 – 7.26 (m,
4H), 6.09 (dd, J = 9.9, 3.7 Hz, 1H), 4.35-4.29 (dd, J = 13.9, 7.4
Hz, 1H), 4.17 – 4.12 (m, 1H), 2.52 – 2.34 (m, 4H), 2.22 – 2.06
(m, 2H), 2.01 – 1.62 (m, 4H), 1.43 – 0.798 (m, 4H); 13C NMR
(100 MHz, CDCl3) δ 204.4, 203.0, 146.5, 145.6, 144.5, 144.1,
138.7, 130.3, 130.1, 129.6, 129.1, 128.9, 127.7, 127.6, 125.5,
125.4, 124.1, 124.1, 88.8, 87.4, 87.2, 43.1, 42.8, 41.0, 40.1,
30.9, 30.0, 29.7, 27.3, 29.1, 27.9, 27.8, 26.6, 26.6, 26.1, 26.0,
26.0, 25.8.
(1'S, 5S)-5-cyclohexyl-4, 5-dihydro-2'H, 3H-spiro [furan-2,
1'-naphthalen]-2'-one (j1). Elution with 1% ethyl acetate in
petroleum ether afforded yellow liquid (6.4 mg, 0.023 mmol,
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