Toluene → HCID 70855539, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, butyl lithium (1.6M, 840 μL, 1.34 mmol) was added at −78° C. to a solution of 4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2-methyl-1,3-thiazole (13a) (260 mg, 1.12 mmol) in anhydrous tetrahydrofuran (5 mL). After 30 minutes, ethyl glyoxylate 50% in toluene (500 μL, 2.5 mmol) was added at −78° C. and the mixture was stirred for 2 hours, hydrolyzed with water and concentrated in vacuo. The residue was diluted with ethyl acetate (20 mL) and the organic layer was washed with water (10 mL), brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired alcohol (13b) as a white solid (90 mg, 0.27 mmol, 24%).

Provenance & Evidence