Benzyl Bromide → HCID 14814224, compound

Participants

Reaction Steps

A 60% suspension of sodium hydride in oil (1.34 g, 33 mmol) was washed with hexane (2×20 ml) under an atmosphere of dry nitrogen. After decanting the hexane the solid was suspended in dry N,N-dimethylformamide (20 ml) and treated with a solution of (S)-1,4-dihydroxy-2-(methoxymethoxy)butane (2 g, 13 mmol) in N,N-dimethylformamide (5 ml). After stirring at room temperature for 6 hours the mixture was treated with a solution of benzyl bromide (3.9 ml, 33 mmol) in N,N-dimethylformamide (5 ml) and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate (100 ml) and water (50 ml). The organic phase was washed with water (2×50 ml), dried with MgSO4 and the solvent removed to give an oil which was chromatographed on silica eluting with ethyl acetate-hexane 1:2 to give (S)-1,4-dibenzyloxy-2-(methoxymethoxy)butane (3.6 g, 82%), [α]D25 -16.0° (c 1.6 in ethanol); IR: υmax (film) 3080, 3060, 3030, 2920, 2890, 2860, 1495, 1450, 1360, 1210, 1155, 1100, 1040, 920, 740, 700 cm-1 ; 1H NMR: δH (CDCl3) 1.90 (2H, m, CH2), 3.35 (3H, s, OCH3), 3.60 (4H, m, 2×CH2), 3.90 (1H, m, CH), 4.50 (4H, m, 2×CH2), 4.68 (1H, d, J=7 Hz, CH of CH2), 4.74 (1H, d, J=7 Hz, CH of CH2), 7.30 (10H, m, 2×C6H5); m/z (NH3CI), MH+ 151, MNH4+ 168.

Provenance & Evidence