Nonanoic acid, 9-bromo-2,2-dimethyl-, ethyl ester → 9-Bromo-2,2-dimethylnonan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 9-bromo-2,2-dimethylnonanoate (example 103, step a) (1.27 g) in dry diethyl ether (40 mL) at 0° C. under N2 was added diisobutylaluminium hydride (1 M in toluene, 9.5 mL) dropwise. The reaction mixture was stirred at 0° C. for 1.25 h then quenched by addition of saturated potassium sodium tartrate solution (150 mL). The mixture was stirred for 15 min then extracted with ethyl acetate (×3) then the combined organics were washed with brine, 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 0.56 g.

Provenance & Evidence