The Journal of Organic Chemistry
Page 10 of 15
(23.2 mg, 0.2 mmol) and the crude product was purified by 7d (31.6 mg, 84% yield) as yellow oil. Rf: 0.51
(petroleumether/EtOAc = 15/1).1H NMR (400 MHz, CDCl3) δ
7.96 (d, J = 7.1 Hz, 2H), 7.55 (t, J = 7.4 Hz,1H), 7.45 (t, J = 7.7
Hz, 2H), 5.17 (t, J = 7.9 Hz,1H), 3.02 – 2.97 (m, 2H), 2.42 (q, J
= 7.3 Hz, 2H), 1.69 (s, 3H), 1.64 (s, 3H). 13C {1H} NMR (101
MHz, CDCl3) δ: 200.1, 137.0, 132.9, 132.8, 128.5, 128.2,
128.0, 122.9, 38.7, 25.7, 22.9, 17.7.
(E)-1-(4-methoxyphenyl)-5-phenylpent-4-en-1-one (7e).39d
Target compound was obtained according to General Procedure
with triethylsilane (23.2 mg, 0.2 mmol) and the crude product
was purified by silica gel chromatograph using
petroleumether/EtOAc = 200/1 as eluent to give pure product
7e (48.0 mg, 91% yield) as yellow oil. Rf: 0.6
(petroleumether/EtOAc = 30/1).1H NMR (400 MHz, CDCl3) δ
7.99 (d, J = 9.0 Hz, 2H), 7.41 – 7.27 (m, 4H), 7.21 (t, J = 7.2
Hz,1H), 6.96 (d, J = 8.9 Hz, 2H), 6.48 (d, J = 15.8 Hz,1H), 6.32
(dt, J = 15.8, 6.8 Hz,1H), 3.89 (s, 3H), 3.12 (t, J = 7.4 Hz, 2H),
2.67 (q, J = 6.8 Hz, 2H). 13C {1H} NMR (101 MHz, CDCl3) δ:
197.9, 163.4, 137.5, 130.7, 130.3, 130.0, 129.3, 128.5, 127.0,
126.0, 113.7, 55.4, 37.9, 27.7.
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silica gel chromatograph using petroleumether/EtOAc = 30/1 as
eluent to give pure product 5j (28.3 mg, 82% yield) as yellow
o
solid; m.p. 80.5-69.6 C; Rf: 0.38 (petroleumether/EtOAc =
7/1).1H NMR (400 MHz, CDCl3) δ 7.90 (d, J = 7.9 Hz,1H), 7.58
– 7.52 (m,1H), 7.09 (t, J = 7.1 Hz,1H), 7.01 (d, J = 8.4 Hz,1H),
4.77 – 4.72 (m,1H), 4.62 – 4.56 (m,1H), 4.01 (dd, J = 10.6, 4.9
Hz,1H). 13C {1H} NMR (101 MHz, CDCl3) δ: 182.0, 161.0,
137.4, 128.0, 122.7, 119.1, 118.1, 113.3, 67.3, 39.2.
6-chlorothiochroman-4-one (5k).38f Target compound was
obtained according to General Procedure with triethylsilane
(23.2 mg, 0.2 mmol) and the crude product was purified by
silica gel chromatograph using petroleumether/EtOAc = 30/1 as
eluent to give pure product 5k (37.4 mg, 95% yield) as yellow
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solid; m.p. 69.5.5-70.4 C; Rf: 0.47 (petroleumether/EtOAc =
10/1).1H NMR (400 MHz, CDCl3) δ 7.67 (d, J = 2.4 Hz, 1H),
6.99 – 6.90 (m, 1H), 6.82 (d, J = 8.5 Hz, 1H), 2.86 – 2.83
(m, 2H), 2.59 – 2.56 (m, 2H). 13C {1H} NMR (101 MHz,
CDCl3) δ 192.8, 140.5, 133.2, 131.8, 131.2, 129.0, 128.8,
39.1, 26.5.
(E)-6-phenylhex-5-en-2-one (7f).39e Target compound was
obtained according to General Procedure with triethylsilane
(23.2 mg, 0.2 mmol) and the crude product was purified by
silica gel chromatograph using petroleumether/EtOAc = 200/1
as eluent to give pure product 7f (22.3 mg, 64% yield) as yellow
oil. Rf: 0.48 (petroleumether/EtOAc = 15/1).1H NMR (400
MHz, CDCl3) δ 7.36 – 7.27 (m, 4H), 7.22 (d, J = 7.0 Hz,1H),
6.42 (d, J = 15.8 Hz,1H), 6.20 (dt, J = 15.8, 6.8 Hz,1H), 2.63 (t,
J = 7.2 Hz, 2H), 2.49 (q, J = 7.1 Hz, 2H), 2.18 (s, 3H). 13C {1H}
NMR (101 MHz, CDCl3) δ: 208.0, 137.4, 130.7, 128.8, 128.5,
127.1, 126.0, 43.2, 30.0, 27.1.
(E)-1,5-diphenylpent-4-en-1-one (7a).39a Target compound
was obtained according to General Procedure with
triethylsilane (23.2 mg, 0.2 mmol) and the crude product was
purified
by
silica
gel
chromatograph
using
petroleumether/EtOAc = 200/1 as eluent to give pure product
7a (40.1mg, 85% yield) as yellow solid; m.p. 54.5-54.9 oC;. Rf:
0.51 (petroleumether/EtOAc = 15/1).1H NMR (400 MHz,
CDCl3) δ 7.57 (t, J = 7.4 Hz,1H), 7.47 (t, J = 7.5 Hz, 2H), 7.35
(d, J = 7.1 Hz, 2H), 7.30 (t, J = 7.6 Hz, 2H), 7.20 (t, J = 7.2
Hz,1H), 6.48 (d, J = 15.8 Hz,1H), 6.30 (dt, J = 15.8, 6.8 Hz,1H),
3.15 (t, J = 7.4 Hz, 2H), 2.67 (q, J = 7.4, 7.0 Hz, 2H). 13C {1H}
NMR (101 MHz, CDCl3) δ: 199.3, 137.5, 136.9, 133.1, 130.8,
129.2, 128.6, 128.5, 128.1, 127.1, 126.0, 38.3, 27.5.
(E)-5-(4-chlorophenyl)-1-phenylpent-4-en-1-one(7b).39b
Target compound was obtained according to General Procedure
with triethylsilane (30.2 mg, 0.26 mmol) and the crude product
was purified by silica gel chromatograph using
petroleumether/EtOAc = 200/1 as eluent to give pure product
7b (43.2 mg, 80% yield) as yellow oil. Rf: 0.50
(petroleumether/EtOAc = 15/1).1H NMR (400 MHz, CDCl3) δ
7.97 (d, J = 7.3 Hz, 2H), 7.56 (t, J = 7.4 Hz,1H), 7.46 (t, J = 7.6
Hz, 2H), 7.24 (s, 4H), 6.40 (d, J = 15.8 Hz,1H), 6.26 (dt, J =
15.8, 6.8 Hz,1H), 3.15 (t, J = 7.3 Hz, 2H), 2.64 (q, J = 6.8 Hz,
2H). 13C {1H} NMR (101 MHz, CDCl3) δ: 199.3, 137.0, 136.1,
133.3, 132.8, 130.0, 129.8, 128.78, 128.76, 128.2, 127.4, 38.2,
27.6.
(E)-1-phenyloct-4-en-1-one (7c).39c Target compound was
obtained according to General Procedure with triethylsilane
(23.2 mg, 0.2 mmol) and the crude product was purified by
silica gel chromatograph using petroleumether/EtOAc = 200/1
as eluent to give pure product 7c (33.5 mg, 83%) as yellow oil.
Rf: 0.56 (petroleumether/EtOAc = 30/1).1H NMR (400 MHz,
CDCl3) δ 7.96 (dd, J = 8.3, 1.2 Hz, 2H), 7.55 (t, J = 7.4 Hz,1H),
7.45 (t, J = 7.6 Hz, 2H), 5.48 (t, J = 3.6 Hz, 2H), 3.06 – 3.01 (m,
2H), 2.43 (t, J = 9.5 Hz, 2H), 1.96 (t, J = 9.5 Hz, 2H), 1.39 –
1.33 (m, 2H), 0.87 (t, J = 7.4 Hz, 3H). 13C {1H} NMR (101
MHz, CDCl3) δ: 199.8, 137.0, 132.9, 131.4, 128.6, 128.5,
128.0, 38.6, 34.6, 27.2, 22.6, 13.6.
3-cinnamylpentane-2,4-dione:3-(1-hydroxyethylidene)-6-
phenylhex-5-en-2-one=1:1 (7g).39f Target compound was
obtained according to General Procedure with triethylsilane
(23.2 mg, 0.2 mmol) and the crude product was purified by
silica gel chromatograph using petroleumether/EtOAc = 200/1
as eluent to give pure product 7g (33.7 mg, 78% yield) as yellow
oil. Rf: 0.48 (petroleumether/EtOAc = 7/1).1H NMR (300 MHz,
CDCl3) δ 16.78 (s,1H), 7.37 – 7.19 (m, 11H), 6.45 (d, J = 15.8
Hz,1H), 6.32 (s,1H), 6.21 (d, J = 15.9 Hz,1H), 6.07 (d, J = 15.8
Hz,1H), 3.80 (t, J = 7.3 Hz,1H), 3.16 (d, J = 5.2 Hz, 2H), 2.75
(t, J = 7.2 Hz, 2H), 2.21 (s, 6H), 2.16 (s, 6H). 13C {1H} NMR
(101 MHz, CDCl3) δ: 203.8, 191.7, 137.2, 136.9, 132.9, 130.3,
128.72, 128.69, 127.8, 127.7 127.5, 126.3, 126.2, 125.6, 68.5,
31.7, 30.6, 29.5, 23.2, 1.2.
methyl (E)-2-acetyl-5-phenylpent-4-enoate (7h).39d Target
compound was obtained according to General Procedure with
triethylsilane (23.2 mg, 0.2 mmol) and the crude product was
purified
by
silica
gel
chromatograph
using
petroleumether/EtOAc = 200/1 as eluent to give pure product
7h (41.2 mg, 89% yield) as yellow oil. Rf: 0.48
(petroleumether/EtOAc = 7/1).1H NMR (400 MHz, CDCl3) δ
7.32 – 7.25 (m, 4H), 7.21 (d, J = 6.9 Hz,1H), 6.45 (d, J = 15.8
Hz,1H), 6.10 (dt, J = 15.7, 7.2 Hz,1H), 3.73 (s, 3H), 3.60 (t, J =
7.4 Hz,1H), 2.74 (t, J = 7.3 Hz, 2H), 2.25 (s, 3H). 13C {1H}
NMR (101 MHz, CDCl3) δ: 202.3, 169.7, 136.9, 132.8, 128.5,
127.4, 126.2, 125.6, 59.4, 52.5, 31.5, 29.3.
5-cinnamyl-2,2-dimethyl-1,3-dioxane-4,6-dione
(7i).39g
5-methyl-1-phenylhex-4-en-1-one (7d).39d Target compound
was obtained according to General Procedure with
triethylsilane (23.2 mg, 0.2 mmol) and the crude product was
Target compound was obtained according to General Procedure
with triethylsilane (23.2 mg, 0.2 mmol) and the crude product
was purified by silica gel chromatograph using
petroleumether/EtOAc = 200/1 as eluent to give pure product
7i (46.3 mg, 89% yield) as yellow oil. Rf: 0.50
purified
by
silica
gel
chromatograph
using
petroleumether/EtOAc = 200/1 as eluent to give pure product
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