Water → HCID 86628703, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of ethyl glycolate (374 μl, 3.957 mmol) and biphenyl-4-sulfonyl chloride (1 g, 3.957 mmol) in anhydrous diethyl ether (2 ml) at 0° C. was treated dropwise with triethylamine (1.1 ml, 7.914 mmol). The temperature was maintained at 0° C. with stirring for a further 2 h. After this time, water was added and the phases separated. The aqueous phase was extracted with fresh diethyl ether. The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo. The crude product was purified by column chromatography over silica gel (Rf=0.26, 25% ethyl acetate in hexane) affording 16 as a colourless oil (1.055 g, 83%). δH (400 MHz, CDCl3) 1.25 (3H, t, J=6.8 Hz, CH3), 4.20 (2H, q, J=6.8 Hz, CH2), 4.65 (2H, s, CH2), 7.44-7.51 (3H, m, ArH), 7.61 (2H, d, J=7.6 Hz, ArH), 7.76 (2H, d, J=8 Hz, ArH), 8.01 (2H, d, J=8 Hz, ArH); δc (100.6 MHz, CDCl3) 14.2, 62.2, 65.0, 127.6, 128.1, 128.9, 129.0, 129.4, 134.4, 139.2, 147.4, 166.2; MS (ES+) 338.1 (100%, [M+H2O]+).

Provenance & Evidence