Ammonium Chloride → 1-Cyclopropyl-5-fluoroindan-1-ol

Participants

Reaction Steps

To a solution of 5-fluoroindanone (0.95 g, 6.33 mmol) in anhydrous ether (30 ml) under nitrogen at room temperature add cyclopropyl magnesium bromide (9.1 ml, 7.28 mmol, 1.15 equivalents, 0.80 M in tetrahydrofuran) dropwise while maintaining a gentle reflux. After stirring overnight, quench the reaction at room temperature via dropwise addition of 10% aqueous ammonium chloride. Dilute the reaction with ether, wash with water (2×), dry over anhydrous sodium sulfate, filter, and concentrate to give the title compound (1.30 g, ˜100%). NMR (CDCl3, 400 MHz): δ 0.26 (m, 1H), 0.36-0.51 (m, 3H), 1.21 (m, 1H), 2.13 (m, 1H), 2.28 (m, 1H), 2.80 (m, 1H), 2.95 (m, 1H), 6.88 (m, 2H), 7.29 (m, 1H).

Provenance & Evidence