Ethanol → HCID 131729098, compound

Participants

Reaction Steps

Following the general procedure for the preparation of carboxylic esters from carboxylic acids of Description 15, (2R/S)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoic acid (14) (0.5 g, 1.2 mmol) dissolved in 5 mL of anhydrous dichloromethane (DCM) was reacted with 0.14 mL (0.2 g, 0.14 mmol) of oxalyl chloride. After the reaction was complete, a solution of 5 mL of ethanol (EtOH) and 0.16 mL of pyridine (0.15 g, 1.9 mmol) 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) (EtOAc/Hxn=1:2) as eluent to provide 0.31 g (58% yield) of the title compound (23a) as a colorless oil. Rf=0.59 (EtOAc/Hxn=1:2). 1H NMR (400 MHz, CDCl3): δ=1.05 (s, 3H), 1.06 (s, 3H), 1.33 (t, J=6.8 Hz, 3H), 2.25-2.33 (m, 2H), 3.22-3.26 (m, 2H), 3.65-3.68 (m, 2H), 3.81 (s, 1H), 3.82 (s, 3H), 3.97 (d, J=9.2 Hz, 1H), 4.19-4.31 (m, 4H), 4.56 (d, J=11.2 Hz, 1H), 6.88 (d, J=8.4 Hz, 2H), 7.26 (d, J=9.2 Hz, 2H) ppm. MS (ESI) m/z 458.97 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence