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

HRID 5563
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HRID 5563 반응식
[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]
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 2

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

시약·촉매·용매 1

HCID 12679Hexamethylphosphoramide용매

실험 절차

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).

출처 및 근거

ORD 기록
ord-85107b868f4343088910de19a024cbd4
출처 데이터셋
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05244910

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