Dimethyl Sulfoxide → HCID 10931516, compound

Participants

Reaction Conditions

Reaction Steps

A solution of dimethyl sulfoxide (18.7 ml, 260 mmol) in 80 ml of dichloromethane is added dropwise within 5 min to a stirred solution of oxalyl chloride (11 ml, 130 mmol) in 400 ml of dichloromethane cooled to −78° C. The mixture is stirred for 10 min at −70° C. A solution of (E)-2,2-Dimethyl-3-ethyl-3-penten-1-ol 24 (15.57 g, 110 mmol) in 60 ml of dichloromethane is added dropwise within 5 min. The mixture is stirred for 1 h at −70° C. The reaction is quenched by dropwise addition of triethyl amine (76.3 ml, 550 mmol). The mixture is warmed to r.t. within 45 min. Water (400 ml) is added and the mixture is stirred for 10 min. The organic layer is separated off, and the aqueous layer is extracted with diethyl ether (3×200 ml). The combined organic extracts are dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by vacuum distillation affords the title compound 25 (9.7 g, 63%) as a colourless liquid (b.p. 85-86° C./28 mbar). 13C-NMR (100 MHz, CDCl3): δ=203.5; 141.4; 122.6; 52.7; 24.2; 20.9; 14.1; 13.8

Provenance & Evidence