Benzyl mercaptan → HCID 69437475, compound

Sodium (0.268 g, 11.6 mmol) was dissolved in ethanol (25 mL) and the resulting solution was treated with benzyl mercaptan (1.87 mL, 15.9 mmol). The reaction mixture was cooled on ice and the 2,2-bis-methylsulfonyloxymethyl-malonic acid diethyl ester (2.00 g, 5.31 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours and then heated at 55° C. for 1.5 hours. The resulting solution was cooled to room temperature and poured into ice water. The product was extracted with ethyl acetate. The extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure and the residue was chromatographed on silica gel eluting with ethyl acetate/hexane to give 3-benzylsulfanyl-2-benzylsulfanylmethyl-propionic acid ethyl ester (1.589 g, 83% yield).

1. temperatureThe reaction mixture was cooled on ice
2. temperatureheated at 55° C. for 1.5 hours
3. temperatureThe resulting solution was cooled to room temperature
4. extractionThe product was extracted with ethyl acetate
5. washThe extracts were washed with saturated aqueous sodium chloride
6. dry with materialdried over magnesium sulfate
7. customThe solvent was removed by rotary evaporation at reduced pressure
8. customthe residue was chromatographed on silica gel eluting with ethyl acetate/hexane

ORD record

ord-d0c748d9d2564065b26cf34c09564657

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07064123B1