Sodium Carbonate → HCID 10453585, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoromethanesulfonic anhydride, 5.5 mL (32.5 mmol.), was added to 14 mL dry methylene chloride under argon at room temperature. The solution was cooled to -40° C. and 2.3 g (22 mmol.) of finely powdered, oven dried Na2CO3 was added. To the stirred mixture 6.7 g (25 mmol.) of 5-(hydroxymethyl)-4,5-dihydro-3,3-diphenyl-2(3H)furanone in 15 mL of methylene chloride was added dropwise, stirring 2 hours at -40° C. before warming to 0° C. for 0.5 hours. The reaction was quenched at 0° C. by adding 10 mL of water dropwise with vigorous stirring. The layers were separated, the organics washed with brine, dried (MgSO4), and evaporated at reduced pressure to a solid. This material was used as received and usually contained 5 to 15% of unreacted alcohol. 1H NMR (CDCl3)δ 2.77-2.83 (m, 1H), 3.05-3.14 (m, 1H), 4.51-4.71 (m, 2H), 4.7-4.75 (m, 1H), 7.25-7.45 (m, 10H).

Provenance & Evidence