2(3H)-Furanone, 3-bromodihydro- → 3-(4-Chlorobenzenesulfonyl)-dihydro-furan-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of α-bromo-γ-butyrolactone (1.58 g; 9.62 mmol) and 4-chlorobenzenesulfinic acid sodium salt (2.39 g; 12.03 mmol) in ethanol (75 mL) was heated at 65° C. for 10 hours and the volatiles removed in vacuo. The residue was diluted with ethyl acetate and filtered. Removal of the volatiles from the filtrate provided as residue which was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. Removal of the volatiles from the product-rich fractions provided 1.58 g of the desired product. 1H NMR (CDCl3) δ 7.89 (d, 2H), 7.58 (d, 2H), 4.54 (m, 1H), 4.42 (m, 1H), 4.03 (dd, 1H), 3.07 (m, 1H), 2.77 (m, 1H).

Provenance & Evidence