Sodium Bicarbonate → 2-(3-Amino-phenylmethanesulfonyl)-ethanol

Participants

Reaction Steps

Titanium(III)chloride solution (about 15%) in about 10% hydrochloric acid (MERCK (MDA) INCL SCHUCHARDT, 114 ml) was added to a stirred solution of 2-[(3-nitrobenzyl)sulfonyl]ethanol (9.0 g; 36.7 mmol) in THF (384 ml) at room temperature and the batch was stirred for 18 hours. By adding aqueous sodium bicarbonate solution the pH value of the reaction mixture was raised to 7-8 before the batch was extracted with ethyl acetate (2×). The combined organic phases were washed with brine, dried (Sodium sulfate), filtered and concentrated. The residue was purified by column chromatography (DCM/ethanol 95:5) to give the desired product.

Provenance & Evidence