4-Toluenesulfonyl chloride → (S)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

To a stirred solution of (S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one (2.0 g, 17.2 mmol) in DCM (20 mL) was added Et3N (4.8 mL, 34.44 mmol) followed by p-toluenesulfonyl chloride (3.61 g, 18.94 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred at the same temperature for 15 h. The reaction mixture was quenched with water (100 mL) and extracted with DCM (2×50 mL). The combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 50% EtOAc/hexane as eluent) to provide compound A94-1 (4.06 g, 87%) as a white solid.

1. customThe reaction mixture was quenched with water (100 mL)
2. extractionextracted with DCM (2×50 mL)
3. washThe combined organic layers were washed with water (50 mL), brine (50 mL)
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography (silica gel, 50% EtOAc/hexane as eluent)
7. customto provide compound A94-1 (4.06 g, 87%) as a white solid

ORD record

ord-df0627019ac24a48bb2277483d672be2

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365522B2