Methanol → 3-(4,4'-Dimethoxytrityloxymethyl)benzylamine

Participants

Reaction Steps

To a suspension of LiAlH4 (238 mg, 6.28 mmol) in diethyl ether (30 mL), which was stirred and cooled with ice, was added dropwise a solution of 3-(4,4′-dimethoxytrityloxymethyl)benzonitrile (4) (0.86 g, 1.98 mmol) in diethyl ether (90 mL). The mixture was stirred for 16 hours at a room temperature under Ar atmosphere. TLC was used to confirm there was no starting material in the reaction mixture. Then, to the mixture were added water (1.2 mL) and MeOH (7.2 mL) and stirred for additional 30 minutes. Then, a formed salt was removed by suction filtration. The filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=100:1) to give 3-(4,4′-dimethoxytrityloxymethyl)benzylamine (5) (0.58 g, 69%) as a colorless oil.

Provenance & Evidence