Lithium → HCID 13687921, compound

Participants

Reaction Steps

0.3 g (0.9 mmol) of isopropyl 6-[1-hydroxy-1-(4-methyl-3-pyridyl)methyl]-2-napthoate in 5 ml of absolute tetrahydrofuran is added, at 0° C., to 38 mg (1 mmol) of lithium alanate in 1 ml of absolute tetrahydrofuran, and the mixture is then stirred at room temperature (24 h). After addition of a further 40 mg (1 mmol) of lithium alanate the mixture is stirred at room temperature for 24 h. Excess lithium alanate is destroyed with 2 N HCl, and the solution is neutralized with sodium bicarbonate solution. It is extracted with ethyl acetate, and this is evaporated, and the residue is chromatographed on silica gel using ethyl acetate/methanol 4:1. 0.16 g (65%) of 1-(6-hydroxymethyl-2-naphthyl)-1-(4-methyl-3-pyridyl)methanol is obtained. Melting point 151°-3° C.

Provenance & Evidence