Benzyl Alcohol → HCID 86629042, compound

Participants

Reaction Steps

Following the general procedure for the preparation of carboxylic esters from carboxylic acids of Description 15, (2R)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoic acid (13) (0.50 g, 1.2 mmol) dissolved in 20 mL of anhydrous dichloromethane (DCM) was reacted with 0.7 mL (1.4 mmol) of oxalyl chloride (2.0 M in DCM). After completion of the reaction, a solution of 0.34 mL of benzyl alcohol (0.34 mL, 0.36 g, 3.3 mmol) and 0.28 mL of pyridine (0.26 g, 3.3 mmol) in 10 mL of anhydrous dichloromethane (DCM) was added to the acid chloride. After work-up, the crude material was purified by silica gel column chromatography using a mixture of ethyl acetate (EtOAc) and hexane (Hxn) as eluent (EtOAc/Hxn=1:2) to provide 0.44 g (74% yield) of the title compound (31a) as a colorless oil. Rf=0.47 (EtOAc/Hxn=1:2). 1H NMR (400 MHz, CDCl3): δ=1.02 (s, 6H), 2.22-2.29 (m, 2H), 3.18-3.22 (m, 2H), 3.45 (t, J=6.4 Hz, 2H), 3.81 (s, 3H), 3.84 (s, 1H), 3.93 (d, J=9.2 Hz, 1H), 4.17 (d, J=9.2 Hz, 1H), 4.27 (d, J=11.2 Hz, 1H), 4.53 (d, J=10.8 Hz, 1H), 5.20 (s, 2H), 6.85 (d, J=8.8 Hz, 2H), 7.21 (d, J=8.8 Hz, 2H), 7.35-7.40 (m, 5H) ppm. MS (ESI) m/z 521.16 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence