UPDATES
EtOAc 100/0 to 80/20; Rf =0.45 (Cyclohexane/EtOAc:
70/30).
dione 3z (100 mg, 0.40 mmol). The title compound was
1
2
3
obtained after flash chromatography as yellow liquid; yield
1
78% (73.6 mg); H NMR (400 MHz, CDCl3) d 7.03 (d, J=
8.5 Hz, 2H), 6.78 (d, J=8.5 Hz, 2H), 3.70 (s, 3H), 3.53 (s,
2H), 3.33–2.86 (m, 5H), 2.38 (t, J=7.2 Hz, 2H), 1.55–1.48 (m,
4H); 13C NMR (101 MHz, CDCl3) d 208.58, 158.69, 130.42,
126.44, 114.19, 72.43, 58.52, 55.28, 49.25, 41.47, 29.01, 20.50;
FT-IR (neat, cmÀ1): 1713, 1613, 1598, 1573, 1513, 1464, 1408,
1363, 1301, 1248, 1178, 1119, 1080, 1036; HRMS (ESI
positive, m/z): found 259.1310 ([M+Na]+), calc. for C13H20O3
Na (M+Na): 259.1310; Flash chromatography conditions:
Cyclohexane/EtOAc 90/10 to 70/30; Rf =0.60 (Cyclohexane/
EtOAc: 70/30).
4
5
6
7
8
9
10
11
12
13
14
15
N-(4-(2-Oxooctyl)phenyl)acetamide (4w)
Compound 4w was prepared according to the general
procedure using N-(4-(2-oxooctanoyl)phenyl)acetamide 3w
(100 mg, 0.3632 mmol). The title compound was obtained
after flash chromatography as brown liquid; yield 98%
1
(93.0 mg); H NMR (300 MHz, CDCl3) d 7.45 (d, J=8.3 Hz,
2H), 7.14 (d, J=8.3 Hz, 2H), 3.63 (s, 2H), 2.43 (t, J=7.4 Hz,
2H), 2.17 (s, 3H), 1.61–1.46 (m, 2H), 1.35–1.02 (m, 6H), 0.85
(t, J=6.7 Hz, 3H); 13C NMR (75 MHz, CDCl3) d 209.05,
168.64, 136.94, 130.06, 129.87, 120.21, 49.41, 42.11, 31.53,
28.77, 24.44, 23.72, 22.45, 14.00; FT-IR (neat, cmÀ1): 1712,
1668, 1603, 1538, 1514, 1467, 1412, 1371, 1319, 1264, 1178,
1-(Quinolin-6-yl)octan-2-one (4za)
16 1128, 1066; HRMS (ESI positive, m/z): found 262.1802 ([M+
Compound 4za was prepared according to the general
procedure using 1-(quinolin-6-yl)octane-1,2-dione 3za
(100 mg, 0.37 mmol). The title compound was obtained after
flash chromatography as yellow liquid; yield 65% (61.6 mg);
1H NMR (300 MHz, CDCl3) d 8.89 (d, J=4.2 Hz, 1H), 8.29–
7.92 (m, 2H), 7.64 (s, 1H), 7.55 (d, J=8.6, 1H), 7.40–7.36 (m,
1H), 3.87 (s, 2H), 2.49 (t, J=7.4 Hz, 2H), 1.95–1.42 (m, 2H),
1.28–1.22 (m, 6H), 0.83 (t, J=6.6 Hz, 3H); 13C NMR
(75 MHz, CDCl3) d 208.01, 150.28, 147.41, 135.73, 132.80,
131.22, 129.78, 128.30, 127.90, 121.33, 49.79, 42.39, 31.52,
28.77, 23.70, 22.43, 13.96; FT-IR (neat, cmÀ1): 1712, 1622,
1595, 1572, 1501, 1466, 1406, 1379, 1366, 1325, 1119, 1065,
1032, 957; HRMS (ESI positive, m/z): found 256.1707 ([M+
H]+), calc. for C17H22NO (M+H): 256.1701; Flash chroma-
tography conditions: Cyclohexane/EtOAc 100/0 to 70/30; Rf
= 0.65 (Cyclohexane/EtOAc: 50/50).
H]+), calc. for C16H23NO2 (M+H): 262.1807; Flash chroma-
17
tography conditions: Cyclohexane/EtOAc 70/0 to 50/50; Rf =
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
0.55 (Cyclohexane/EtOAc: 50/50).
1-(Naphthalen-2-yl)octan-2-one (4x)
Compound 4x was prepared according to the general
procedure using 1-(naphthalen-2-yl)octane-1,2-dione 3x
(100 mg, 0.37 mmol). The title compound was obtained after
flash chromatography as yellow liquid; yield 92% (87.2 mg);
1H NMR (400 MHz, CDCl3) d 7.75–7.61 (m, 3H), 7.54 (s,
1H), 7.40–7.30 (m, 2H), 7.20 (d, J=8.4 Hz, 1H), 3.69 (s, 2H),
2.34 (t, J=7.4 Hz, 2H), 1.50–1.40 (m, 2H), 1.17–1.03 (m, 6H),
0.73 (t, J=6.7 Hz, 3H); 13C NMR (101 MHz, CDCl3) d
208.49, 133.62, 132.46, 132.01, 128.35, 128.10, 127.69, 127.62,
127.52, 126.19, 125.77, 50.29, 42.09, 31.58, 28.81, 23.75, 22.48,
14.01; FT-IR (neat, cmÀ1): 1713, 1632, 1600, 1509, 1466, 1406,
1260, 1126, 1069, 1017, 959, 908; HRMS (ESI positive, m/z):
found 255.1749 ([M+H]+), calc. for C18H23O (M+H):
255.1749; Flash chromatography conditions: Cyclohexane/
EtOAc 100/0 to 98/2; Rf =0.70 (Cyclohexane/EtOAc: 95/5).
(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-((4-(2-oxooc-
tyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-Triyl
triacetate (4zb)
Compound 4zb was prepared according to the general
procedure using (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-
(2-oxooctanoyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl
triacetate 3zb (100 mg, 0.1722 mmol). The title compound
was obtained after flash chromatography as yellow liquid;
6-Hydroxy-1-(4-methoxyphenyl)hexan-2-one (4y)
Compound 4y was prepared according to the general
procedure using 6-hydroxy-1-(4-methoxyphenyl)hexane-1,2-
dione 3y (100 mg, 0.42 mmol). The title compound was
obtained after flash chromatography as colorless liquid; yield
25
yield 50% (48.8 mg); [a]D À11 (c, 0.55 in CH2Cl2); 1H NMR
(400 MHz, CDCl3) d 7.45 (d, J=8.1 Hz, 2H), 7.14 (d, J=
8.1 Hz, 2H), 5.22 (t, J=9.3 Hz, 1H), 5.04 (t, J=9.8 Hz, 1H),
4.97 (t, J=9.7 Hz, 1H), 4.69 (d, J=10.1 Hz, 1H), 4.29–4.12
(m, 2H), 3.75–3.70 (m, 1H), 3.68 (s, 1H), 2.46 (t, J=7.4 Hz,
2H), 2.08 (s, 6H), 2.02 (s, 3H), 1.99 (s, 3H), 1.58–1.54 (m,
2H), 1.28–1.24 (m, 6H), 0.86 (t, J=6.8 Hz, 3H). 13C NMR
(101 MHz, CDCl3) d 207.99, 170.67, 170.27, 169.50, 169.36,
134.95, 133.51, 130.42, 130.17, 86.01, 75.98, 74.12, 70.12,
68.38, 62.29, 49.57, 42.53, 31.69, 28.93, 23.85, 22.60, 20.87,
20.71, 14.14; FT-IR (neat, cmÀ1): 2930, 1756, 1713, 1603, 1367,
1248, 1214, 1037, 915; HRMS (ESI positive, m/z): found
589.2083 ([M+Na]+), calc. for C28H38O10SNa (M+Na):
589.2078; Flash chromatography conditions: Cyclohexane/
EtOAc 70/30 to 50/50; Rf =0.30 (Cyclohexane/EtOAc:
50/50).
1
80% (75.3 mg); H NMR (300 MHz, CDCl3) d 7.11 (d, J=
8.5 Hz, 2H), 6.86 (d, J=8.6 Hz, 2H), 3.79 (s, 3H), 3.61 (s,
2H), 3.11 (t, J=6.7 Hz, 2H), 2.45 (t, J=7.0 Hz, 2H), 1.99–
1.49 (m, 4H); 13C NMR (75 MHz, CDCl3) d 208.06, 158.70,
130.36, 126.16, 114.22, 55.28, 49.30, 40.30, 32.72, 24.55, 6.08;
FT-IR (neat, cmÀ1): 1710, 1611, 1583, 1511, 1462, 1406, 1301,
1245, 1177, 1112, 1032; HRMS (ESI positive, m/z): found
223.1340 ([M+H]+), calc. for C13H19O3 (M+H): 223.1334;
Flash chromatography conditions: Cyclohexane/EtOAc 70/30
to 50/50; Rf =0.45 (Cyclohexane/EtOAc: 70/30).
6-Methoxy-1-(4-methoxyphenyl)hexan-2-one (4z)
Compound 4z was prepared according to the general
procedure using 6-methoxy-1-(4-methoxyphenyl)hexane-1,2-
Adv. Synth. Catal. 2017, 359, 1–11
8
ꢀ 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ÞÞ
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