7
1
3
CDCl ): δ = 201.7, 170.3, 133.1, 129.4, 129.1,
A
12
C
8.
C
1,
E
80
P
.9
T
, 2
E
6
D
.1, MA
C
N
N
U
M
S
R
C
(
R
10
I
0
P
MHz, CDCl ): δ = 204.7, 169.8, 147.8, 147.5,
3
T
3
+
2
0.7; HRMS (ESI-TOF) calcd for [C H O +Na] 215.0679,
133.4, 120.3, 108.3, 106.9, 101.1, 71.4, 49.8, 30.4, 21.1; HRMS
(ESI-TOF) calcd for [C H O +Na] 273.0733, found 273.0735.
11
12
3
+
found 215.0676.
13
14
5
4
.2.28.
1-(tert-Butyldiphenylsilyloxy)-1-phenylpropan-2-one
4.2.34. 1-(Naphthalen-1-yl)-3-oxobutyl benzoate (4j). Isolated
yield of 4j, (94.2 mg, 74%). Colorless oil; IR (CHCl ): ν =
max
(4d). Isolated yield of 4d, (141.3 mg, 91%). Colorless oil; IR
3
(
CHCl ): ν = 3070, 2961, 2932, 2894, 2859, 1717, 1589, 1492,
3062, 3009, 2925, 2854, 1719, 1601, 1584, 1510, 1492, 1451,
1417, 1398, 1363, 1315, 1270, 1176, 1110, 1070, 1058, 1026,
975, 938, 862, 798, 713, 686 cm ; H NMR (400 MHz,
3
max
1
8
7
7
472, 1428, 1391, 1351, 1307, 1190, 1113, 1070, 1028, 910, 855,
-
1
1
–1
1
23, 701, 648 cm ; H NMR (400 MHz, CDCl /TMS): δ =
3
.66−7.64 (m, 2H), 7.47−7.42 (m, 3H), 7.40−7.32 (m, 5H),
CDCl /TMS): δ = 8.25 (d, J = 8.4 Hz, 1H), 8.10–8.07 (m, 2H),
3
13
.31−7.27 (m, 5H), 5.08 (s, 1H), 2.02 (s, 3H), 1.13 (s, 9H);
C
7.88 (d, J = 7.6 Hz, 1H), 7.80 (d, J = 8.2 Hz, 1H), 7.64–7.42 (m,
7H) 7.21 (dd, J = 9.0, 4.0 Hz, 1H), 3.40 (dd, J = 16.9, 8.6 Hz,
NMR (100 MHz, CDCl ): δ = 207.7, 138.2, 135.7, 135.6, 132.8,
3
13
1
2
4
32.6, 130.0, 129.8, 128.5, 128.1, 127.8, 127.6, 126.2, 81.7, 26.9,
1H), 3.13 (dd, J = 16.9, 4.1 Hz, 1H), 2.23 (s, 3H); C NMR (100
+
4.3, 19.3; HRMS (ESI-TOF) calcd for [C H O Si+Na]
MHz, CDCl ): δ = 204.7, 165.4, 135.6, 133.9, 133.1, 130.1,
25
28
2
3
11.1751, found 411.1755.
129.9, 129.7, 129.0, 128.8, 128.4, 126.6, 125.8, 125.3, 123.7,
1
23.0, 69.9, + 49.7, 30.5; HRMS (ESI-TOF) calcd for
4
.2.29. 4-(tert-Butyldiphenylsilyloxy)-4-phenylbutan-2-one (4e).
[
C H O +Na] 341.1148, found 341.1148.
21
18
3
Isolated yield of 4e, (135.5 mg, 84%). Colorless oil; IR (CHCl3):
νmax = 3070, 2999, 2931, 2894 2858, 1716, 1589, 1472, 1454,
4.2.35.
4-(Benzyloxy)-4-(4-nitrophenyl)butan-2-one (4k).
1
9
427, 1391, 1361, 1309, 1259, 1190, 1161, 1111, 1028, 1007,
56, 912, 855, 822, 701, 613 cm ; H NMR (400 MHz,
Isolated yield of 4k, (89.8 mg, 75%). Colorless oil; IR (CHCl3):
νmax = 3066, 3032, 3008, 2865, 1716, 1606, 1521, 1497, 1415,
1347, 1162, 1096, 1075, 1028, 884, 857, 699 cm ; H NMR (400
-
1
1
–1 1
CDCl /TMS): δ = 7.65–7.63 (m, 2H), 7.44–7.40 (m, 3H), 7.38–
3
7
.32 (m, 3H), 7.25–7.18 (m, 7H), 5.15 (t, J = 6.5 Hz, 1H), 2.92
MHz, CDCl /TMS): δ = 8.15 (d, J = 8.8 Hz, 2H), 7.48 (d, J = 8.7
3
(
(
1
1
dd, J = 15.2, 6.5 Hz, 1H), 2.71 (dd, J = 15.2, 6.4 Hz, 1H), 1.90
Hz, 2H), 7.27–7.21 (m, 5H), 4.93 (dd, J = 8.4, 4.6 Hz, 1H), 4.32
(d, J = 11.3 Hz, 1H), 4.27 (d, J = 11.3 Hz, 1H), 2.99 (dd, J =
16.5, 8.5 Hz, 1H), 2.57 (dd, J = 16.5, 4.6 Hz, 1H), 2.08 (s, 3H);
13
s, 3H), 1.01 (s, 9H); C NMR (100 MHz, CDCl ): δ = 206.4,
3
43.5, 135.8, 133.7, 133.2, 129.7, 129.5, 128.1, 127.5, 127.4,
13
27.3, 126.2, 72.3, 54.1, 31.1, 26.9, 19.2; HRMS (ESI-TOF)
C NMR (100 MHz, CDCl ): δ = 205.4, 148.9, 147.6, 137.2,
3
+
calcd for [C H O Si+Na] 425.1907, found 425.1904.
128.4, 127.9, 127.8, 127.5, 123.9, 76.5, 71.5, 51.5, 30.9; HRMS
26
30
2
+
(
ESI-TOF) calcd for [C H NO +Na] 322.1050, found
17 17 4
4
.2.30. 2-Oxononan-4-yl acetate (4f). Isolated yield of 4f, (73.7
3
22.1049.
mg, 92%). Colorless oil; IR (CHCl ): ν = 3011, 2950, 2932,
3
max
2
1
5
1
1
861, 1736, 1717, 1677, 1628, 1459, 1424, 1364, 1248, 1166,
4.2.36.
(3R,4S)-5-Benzyloxy-3,4-isopropylidenedioxy-2-
–1 1
023, 981, 960, 667 cm ; H NMR (400 MHz, CDCl /TMS): δ =
pentanone (4l). Isolated yield of 4l, (55 mg, 52%). Colorless oil;
3
25
.21−5.16 (m, 1H), 2.70 (dd, J = 16.2, 7.4 Hz, 1H), 2.57 (dd, J =
[α]D = +23.4 (c = 0.16, CHCl ); IR CHCl : ν = 2988, 2925,
3 3 max
6.2, 5.3 Hz, 1H), 2.13 (s, 3H), 2.0 (s, 3H), 1.54–1.51 (m, 2H),
2862, 1717, 1497, 1454, 1418, 1381, 1371, 1355, 1252, 1166,
1133, 1092, 1026, 911, 858, 699 cm ; H NMR (400 MHz,
13
–1 1
.281.24 (m, 6H), 0.85 (t, J = 6.8 Hz, 3H); C NMR (100 MHz,
CDCl ): δ = 205.8, 170.5, 70.3, 47.9, 34.0, 31.4, 30.3, 24.7, 22.4,
CDCl /TMS): δ = 7.36–7.32 (m, 5H), 4.61 (s, 2H), 4.22–4.19 (m,
3
3
+
2
2
1.0, 13.9; HRMS (ESI-TOF) calcd for [C H O +Na]
23.1305, found 223.1307.
2H), 3.74 (dd, J = 10.6, 2.64 Hz, 1H), 3.64–3.60 (m, 1H), 2.27 (s,
11
20
3
13
3H), 1.47 (s, 3H), 1.43 (s, 3H); C NMR (100 MHz, CDCl ): δ =
3
2
2
2
08.4, 137.8, 128.4, 127.7, 111.1, 81.9, 77.3, 73.6, 70.2, 26.9,
4
.2.31. 3-Oxo-1-phenylbutyl acetate (4g). Isolated yield of 4g,
+
6.5, 26.2; HRMS (ESI-TOF) calcd for [C H O +Na]
15
20
4
(57.8 mg, 70%). Colorless oil; IR (CHCl ): νmax = 3064, 3032,
3
87.1254, found 287.1252.
2
1
927, 2853, 1736, 1721, 1608, 1495, 1454, 1373, 1239, 1163,
-1 1
043, 950, 917, 871, 701, 667 cm ; H NMR (400 MHz,
4.2.37. Acetophenone (6a). Isolated yield of 6a, (39.4 mg, 82%).
Colorless oil; H NMR (400 MHz, CDCl /TMS): δ = 7.97–7.92
(m, 2H), 7.57–7.51 (m, 1H), 7.48–7.41 (m, 2H), 2.59 (s, 3H); C
NMR (100 MHz, CDCl ): δ = 198.1, 137.0, 133.0, 128.5, 128.2,
1
CDCl /TMS): δ = 7.36–7.28 (m, 5H), 6.18 (dd, J = 8.7, 4.9 Hz,
3
3
13
1
1
2
H), 3.12 (dd, J = 16.6, 8.7 Hz, 1H), 2.82 (dd, J = 16.7, 4.9 Hz,
13
H), 2.15 (s, 3H), 2.04 (s, 3H); C NMR (100 MHz, CDCl ): δ =
3
3
04.6, 169.7, 139.5, 128.5, 128.1, 126.3, 71.5, 49.7, 30.3, 20.9;
26.5.
+
HRMS (ESI-TOF) calcd for [C H O +Na] 229.0835, found
2
12
14
3
4
.2.38. 4-Chloroacetophenone (6b). Isolated yield of 6b, (46.3
29.0835.
mg, 75%). Colorless oil; IR (CHCl ): ν = 3018, 2927, 2855,
3
max
4
.2.32. 1-(4-Methoxyphenyl)-3-oxobutyl acetate (4h). Isolated
1687, 1590, 1572, 1488, 1429, 1397, 1358, 1261, 1095, 1013,
–1 1
yield of 4h, (80.4 mg, 85%). Colorless oil; IR (CHCl ): ν
3
1
=
958, 831, 668 cm ; H NMR (400 MHz, CDCl /TMS) δ = 7.89
3
13
3
max
003, 2960, 2936, 2840, 1740, 1729, 1612, 1516, 1464, 1424,
(d, J = 8.6 Hz, 2H), 7.43 (d, = 8.7 Hz, 2H), 2.58 (s, 3H);
C
–1 1
372, 1303, 1177, 1033, 948, 835, 657 cm ; H NMR (400 MHz,
NMR (100 MHz, CDCl ) δ = 196.8, 139.5, 135.4, 129.7, 128.9,
3
CDCl /TMS): δ = 7.29 (d, J = 8.7 Hz, 2H), 6.86 (d, J = 8.7 Hz,
26.5.
3
2
1
2
1
H), 6.13 (dd, J = 8.5, 5.3 Hz, 1H), 3.78 (s, 3H), 3.10 (dd, J =
6.5, 8.5 Hz, 1H), 2.81 (dd, J = 16.5, 5.3 Hz, 1H), 2.14 (s, 3H),
4
.2.39. 4-Methylacetophenone (6c). Isolated yield of 6c, (38.1
mg, 71%). Colorless oil; IR (CHCl ): νmax = 3032, 3005, 2961,
924, 2857, 1682, 1607, 1569, 1429, 1407, 1358, 1269, 1182,
13
3
.01 (s, 3H); C NMR (100 MHz, CDCl ): δ = 204.8, 169.9,
3
2
59.4, 131.6, 128.0, 113.9, 71.3, 55.2, 49.6, 30.4, 21.1; HRMS
-1
1
+
1019, 954, 912, 815, 734 cm ;
CDCl /TMS): δ = 7.86 (d, J = 8.2 Hz, 2H), 7.27 (d, J = 8.0 Hz,
2H), 2.58 (s, 3H), 2.41 (s, 3H); C NMR (100 MHz, CDCl ): δ =
H NMR (400 MHz,
(ESI-TOF) calcd for [C H O +Na] 259.0941, found 259.0948.
13
16
4
3
13
4
.2.33. 1-(Benzo[d][1,3]dioxol-5-yl)-3-oxobutyl acetate (4i).
3
Isolated yield of 4i, (73.1 mg, 73%). Colorless oil; IR (CHCl3):
νmax = 2919, 2852, 1773, 1736, 1660, 1625, 1600, 1503, 1489,
197.9, 143.9, 134.7, 129.2, 128.4, 26.5, 21.6; HRMS (ESI-TOF)
+
calcd for [C H O+Na] 157.0624, found 157.0623.
9
10
–1 1
1
448, 1359, 1239, 1178, 1103, 1037, 977, 929, 804, 788 cm ; H
4
.2.40. 4-tert-Butylacetophenone (6d). Isolated yield of 6d, (63.5
NMR (400 MHz, CDCl /TMS): δ = 6.84–6.75 (m, 3H), 6.09 (dd,
3
mg, 90%). Colorless oil; IR (CHCl ): ν = 2965, 2907, 2871,
3
max
J = 8.5, 5.1 Hz, 1H), 5.94, (s, 2H), 3.27 (dd, J = 16.6, 8.5 Hz,
1
719, 1685, 1607, 1407, 1363, 1271, 1114, 1015, 958, 838, 777,
1
H), 2.80 (dd, J = 16.6, 5.2 Hz, 1H), 2.14 (s, 3H), 2.02 (s, 3H);