HCID 18357646, compound → HCID 18357488, compound

Participants

Reaction Steps

To a stirred solution of 2 g of 2-[2-(1,2-benzisoxazol-3-yl)-phenyl] acetaldehyde in 50 ml of tetrahydrofuran at -78° C. under a nitrogen atmosphere was added 10 ml of a 1 M solution of allyl magnesium bromide in diethyl ether. The solution was warmed to room temperature and stirred for a further 2 h then quenched by addition of 50 ml of saturated aqueous ammonium chloride. The aqueous layer was extracted with 150 ml then 100 ml of dichloromethane and the combined organic extracts dried over sodium sulfate and evaporated to give crude product which was purified by chromatography eluting with 20% ethyl acetate in hexane, affording 1 g of 3-[2-(2-Hydroxy-4-pentenyl)phenyl]-1,2-benzisoxazole, 1H-NMR (200 MHz, CDCl3) d 5.8 (CH=CH2).

Provenance & Evidence