Benzyl Bromide → HCID 54466557, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the above ketone (33) (14.93 g) in dry THF (200 mL) at -78° C. under Ar was added a solution of lithium bis-trimethylsilylamide (55 mL, 1N in THF). After stirring for 20 min benzylbromide (35 mL) was added and the reaction stirred for an additional 6 h at -78° C. then allowed to slowly warm to room temperature. The reaction was taken up in ethyl acetate, washed with 1N HCl, saturated NaCl, dried over MgSO4 and evaporated. The product (34) was obtained by flash chromatography on silica gel eluted with 20 to 25% ethyl acetate in n-hexane (6.09 g, 31%): TLC Rf 0.17 (20% ethyl acetate, n-hexane); 1H NMR (CDCl3) δ1.12 (3H, d, J=7 Hz), 2.0-3.2 (7H, m), 4.18(1H, q), 5.1(2H, s), 5.33(1 H, dd), 5.55(1H, br s), 7.22 (5H, m), 7.32 (5H, s).

Provenance & Evidence