Ethyl 7-bromo-2,2-dimethylheptanoate → 7-Bromo-2,2-dimethylheptan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 7-bromo-2,2-dimethylheptanoate (example 102, step a) (1.5 g) in dry diethyl ether (50 mL) at 0° C. under N2 was added diisobutylaluminium hydride (1M in toluene, 12.5 mL) dropwise. The reaction mixture was stirred at 0° C. for 1 h then quenched by addition of saturated potassium sodium tartrate (150 mL). The mixture was stirred for 1 h then extracted with ethyl acetate (×3). The combined organics were washed with brine and dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with 0-25% ethyl acetate in cyclohexane to give the subtitled compound as a colourless liquid. Yield 1.16 g.

Provenance & Evidence