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

HRID 5563

Reaction equation

HRID 5563 reaction equation
[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]

Participants

7

Reactant 4

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

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).

Sources & evidence

ORD record
ord-85107b868f4343088910de19a024cbd4
Source dataset
uspto-grants-1993_09
Patent number
US05244910

Linked notes

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