Diisobutylaluminumhydride → 8-(tert-Butyldimethylsilyloxy)-2,2-dimethyloctan-1-ol

Participants

Reaction Conditions

Reaction Steps

Ethyl 8-(tert-butyldimethylsilyloxy)-2,2-dimethyloctanoate (example 279, step a) (20 g) in dry ether under nitrogen (300 mL) was cooled to 0° C. in an ice bath then diisobutylaluminium hydride (1M in toluene, 133 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 1 hour then quenched with saturated aqueous potassium sodium tartrate (Rochelle's salt, 400 mL) and stirred overnight. The mixture was extracted with ethyl acetate (3×300 mL) then the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. Purification was by silica gel chromatography eluting with 0-20% ethyl acetate in cyclohexane to afford the subtitled compound as a colourless liquid. Yield 10.11 g.

Provenance & Evidence