Aluminium lithium hydride → [1-(Hydroxymethyl)-4-methylene-cyclohexyl]methanol

Participants

Reaction Conditions

Reaction Steps

To a suspension of LiAlH4 (0.166 g, 4.4 mmol) in anhydrous Et2O (10 mL) stirred a 0° C. was added a solution of Compound 100a (100 mg, 2.08 mmol) in Et2O (10 mL). The reaction mixture was stirred at r.t. for 2 h. Additional 0.5 equivalents of LiAlH4 were added and the reaction was stirred at r.t. for 1 h. Afterwards, it was quenched, by adding THF/H2O (2 mL:1.3 mL), then 2N HCl (30 mL). Extraction with EtOAc, drying over Na2SO4 and evaporation to dryness afforded a crude, that was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Dichloromethane-Methanol gradient from 1:0 to 95:5) to give the title compound as a white solid. Yield: 92.1%.

Provenance & Evidence