Benzyl Bromide → Benzhydryl 4-(2-furyl)-3-oxaoctanoate

HRID 5563

反応式

HRID 5563 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([CH2:25][CH2:26][CH2:27][CH3:28])[O:7][CH2:8][C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:44](Br)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(P(N(C)C)(N(C)C)=O)C>[CH2:44]([C@@H:8]([O:7][C@H:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[CH2:25][CH2:26][CH2:27][CH3:28])[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([CH2:25][CH2:26][CH2:27][CH3:28])[O:7][CH2:8][C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10]

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 20093117Benzhydryl 4-(2-furyl)-3-oxaoctanoate

生成物 2

HCID 20093117Benzhydryl 4-(2-furyl)-3-oxaoctanoateHCID 70062813(2R,4S) benzhydryl 2-Benzyl-4-(2-furyl)-3-oxaoctanoate

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒

実験手順

Using the procedure in example 90 and (4S) benzhydryl 4-(2-furyl)-3-oxaoctanoate (5.0 g, 13.2 mmol), THF (50 mL), sodium bis(trimethylsilyl)amide (1.0M in THF, 14 mL, 14 mmol), and benzyl bromide (1.7 mL, 14 mmol) in 10 mL HMPA gave (2R,4S) benzhydryl 2-Benzyl-4-(2-furyl)-3-oxaoctanoate, 646.6 mg (10%) and 723 mg (12%) of the (2S 4S) diastereomer which was identical to the sample prepared in example 90. (2R,4S) diastereomer: [α]25D -34.8° (c 1.12, CHCl3); 1H NMR (300 MHz, CDCl3) δ 0.78 (t, 3H, J=7 Hz), 1.12 (m, 4H), 1.69 (m, 1H), 1.83 (m, 1H), 2.98 (m, 2H), 4.11 (t, 1H, J=7 Hz), 4.21 (dd, 1H, J=8 Hz), 6.07 (m, 2H), 6.72 (s, 1H), 7.26 (m, 16H); mass spectrum (FAB): 486 (M+NH4).

出典と根拠

ORDレコード
ord-85107b868f4343088910de19a024cbd4
出典データセット
uspto-grants-1993_09
特許番号
US05244910

関連ノート

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