tert-Butyl mercaptan → HCID 70855406, compound

Participants

Reaction Steps

A mixture of methyl 2-bromo-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethylthiophen-3-yl]acetate (32a) (50 mg, 0.126 mmol), cesium carbonate (82 mg, 0.253 mmol) and 2-methyl-2-propanethiol (23 mg, 0.253 mmol) in N,N-dimethylformamide (2 mL) was stirred at room temperature for 5 hours. The reaction mixture was quenched with water (6 mL) and extracted with ethyl acetate (4×5 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 80/20) to provide the desired thio-ether (32b) (28 mg, 0.07 mmol, 55%) as a clear yellow oil.

Provenance & Evidence