2-(BENZO[D]ISOXAZOL-3-YL)ETHANOL synthesis

Yield:57148-90-0 67.8%

Reaction Conditions:

Stage #1: 2-(benzo[d]isoxazol-3-yl)acetic acidwith dimethylsulfide borane complex in tetrahydrofuran at 0 - 20;
Stage #2: with methanol for 4 h;Heating / reflux;

Steps:

AD.i

To a solution of benzo [d]isoxazol-3-yl-acetic (0.86 g, 4.85 mmol) in anhydrous THF (40 mL) was added dropwise borane dimethylsulfide complex (0.58 mL, 10 M, 5.8 mmol) at 0°C. The mixture was allowed to warm to room temperature and was stirred over night. MeOH (10 mL) was carefully added and when the gas evolution ceased, the mixture was heated under gentle reflux for 4 hours. The reaction mixture was concentrated in vacuo and the remainder was dissolved in dichloromethane (20 mL). An aqueous solution of Na2C03 (20 mL) was added and the aqueous layer was extracted with dichloromethane (3 x 20 mL). The combined organic layers were dried over Na(at)S04 and concentrated in vacuo. The crude product was purified by chromatography on silica gel which afforded 537 mg (67.8%) of the title compound. 1³C NMR (125.7 MHz, CDCl3) 8 163.06,156.92, 130.27,123.65, 121.98, 121.65, 110.10, 60.34, 29.01

References:

WO2005/123748,2005,A1 Location in patent:Page/Page column 104-105