Acetone → 6-Hydroxymethylquinoline

Participants

Reaction Conditions

Reaction Steps

Similar to the method described by C. Kaslow and W. Clark, (JOC 18, 55, 1953), to a stirred solution of methyl quinoline-6-carboxylate (10 g, 53 mmol) in THF (200 mL) at 0° C. was added LiAlH4 (1.3 g, 14.9 mmol) by small portion. The resulting mixture was stirred at 0° C. for 2 h then warmed to RT and stirred for 3 h. Acetone (10 mL) was added followed by MgSO4×10H2O. The resulting mixture was stirred for 1.5 h at RT and filtered over a silica pad. Solvents were removed to give the crude quinolin-6-yl-methanol.

Provenance & Evidence