Ethyl Acetate → 3-Chloro-6,7-dihydro-5H-cyclopenta[B]pyridin-7-OL

Participants

Reaction Steps

A solution of acetic acid 3-chloro-6,7-dihydro-5H-[1]pyrindin-7-yl ester (1.57 g, 7.42 mmol) in methanol (35.7 ml) was treated with a solution of sodium hydroxide (1M; 8.9 ml). The mixture was stirred at room temperature for 1.5 hours. The reaction was followed by TLC (silica gel, heptane:ethyl acetate=1:1; UV detection 254 nm). After completion, the reaction mixture was treated with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulphate, then evaporated leaving a dark red liquid (1.15 g, 91% yield) which crystallised on standing. Following NMR the product was pure enough for the next step of the synthesis. MS (ISP): m/z=170 [M+H]+.

Provenance & Evidence