Hydrochloric Acid → (Z)-3-(2-hydroxaminoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)indene

Participants

Reaction Conditions

Reaction Steps

To a suspension of the oxime from Step 3 (2.0 g, 5.9 mmol) in ethanol (35 mL) at 0° C. there was added pyridine-borane (1.1 g, 11.8 mmol) and 12N aqueous HCl (1.48 mL, 17.75 mmol). The mixture was stirred at 0° C. for 1 hour, then warmed to room temperature. Most of the ethanol was evaporated, the residue diluted with water and ethyl acetate (the product as hydrochloride salt remains in the organic phase) and basified with 1N aqueous NaOH. The product obtained from the organic phase was triturated with hexane and filtered to afford the title compound as a yellow solid, mp: 126° C. dec.

Provenance & Evidence