Aluminium lithium hydride → HCID 11470819, compound

Participants

Reaction Steps

Under N2 atmosphere, a solution of (3R*,10S*)-6,6,8,8,10-pentamethyl-1-oxadispiro-[2.0.5.3]dodecan-12-one (5.65 g, 22.6 mmol) in Et2O (10 mL) was added dropwise within 20 min. to a stirred suspension of lithium aluminum hydride (1.29 g, 33.8 mmol) in Et2O (25 mL). The reaction mixture was refluxed for 3 h, and then stirred at room temp. over night, prior to quenching at 0° C. by addition of water (20 mL), followed by aq. HCl (5 N, 20 mL). The organic layer was separated, the aqueous one extracted with Et2O (2×50 mL). The combined organic extracts were washed with water (50 mL) and brine (25 mL), dried (Na2SO4) and concentrated on the rotary evaporator. The resulting residue was purified by silica-gel FC (pentane/Et2O, 4:1, Rf=0.10) to provide (1R*,2S*,4R*)-1,4,7,7,9,9-hexamethylspiro[4.5]decane-1,2-diol (4.82 g, 84%).

Provenance & Evidence