Ethyl Thioglycolate → HCID 67352988, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% in petrolether, 404 mg, 10 mmol) is washed with dry pentane (3×10 mL), then dry THF (30 mL) is added and the suspension is cooled at 0° C. A solution of mercaptoacetic acid ethyl ester (0.445 mL, 4 mmol) in THF (4 mL) is slowly added. After stirring for 0.5 h at 0° C. a solution of trifluoromethanesulfonic acid 2-acetyl-1,4-dimethyl-penta-1,4-dienyl ester (1.16 g, 4 mmol) in THF (4 mL) is slowly added. The mixture is stirred at 0° C. for 0.5 h, then slowly warmed to rt during 15 h. The reaction mixture is partioned between H2O (75 mL) and DCM (100 mL), the aq. phase is basified with 1M aq. NaOH (50 mL) and extracted with DCM (50 mL). The combined organic extracts are dried (Na2SO4), filtered and evaporated. The crude product is purified by reversed phase MPLC (H2O-MeOH gradient) to give 450 mg of 3,5-dimethyl-4-(2-methyl-allyl)-thiophene-2-carboxylic acid ethyl ester; LC-MS: tR=1.10 min, [M+1]+=239.05.

Provenance & Evidence