Sodium hydride → HCID 69067306, compound

Participants

Reaction Steps

A solution of 3-mercaptopropan-1-ol (360 mg, 3.90 mmol) in THF (8 mL) cooled to 0° C. was treated with 60% NaH (86 mg, 2.15 mmol). After warming to room temperature and stirring for 30 minutes, a solution of (R)-toluene-4-sulfonic acid 2-oxotetrahydrofuran-3-yl ester (500 mg, 1.95 mmol) in THF (2 mL) was added. After stirring at room temperature for 60 hours, the reaction mixture was quenched with saturated NaHCO3 and diluted with EtOAc. The organic layer was washed with saturated NH4Cl, saturated NaHCO3, saturated NaCl, dried over Na2SO4 and concentrated under reduced pressure. The residue was chromatographed (2:1 EtOAc/hexanes) to provide the product as colorless oil (155 mg, 45%).

Provenance & Evidence