Tetrahydrofuran → (2-Bromopyridin-3-yl)methanol

Participants

Reaction Steps

Add ethyl chloroformate (3.17 g, 29.28 mmol) to a solution of 2-bromo-3-pyridinecarboxylic acid (5.63 g, 27.89 mmol) and Et3N (2.96 g, 29.28 mmol) in toluene (150 ml) at RT and stir for 1 h., filter and concentrate. Dissolve the residue in THF (93 ml), add to a suspension of LiAlH4 (1.11 g, 29.28 mmol) in THF (37 mmol) dropwise at −78° C. and stir for 30 min. Quench the reaction with saturated aqueous NH4Cl, stir at RT for 1 h, filter through celite, extract with EtOAc, dry over Na2SO4 and concentrate. Purify the residue by column chromatography to produce the desired compound.

Provenance & Evidence