Ethyl Thioglycolate → 1-O-benzyl-3-O-t-butyldimethylsilyl-2-(ethoxycarbonylmethylthio)glycerol

HRID 1636286Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH:10]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[O:11][S:12]([CH3:15])(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([O:29][CH2:30][CH3:31])(=[O:28])CS.[O-]CC.[Na+]>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH:10]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[O:11][S:12][CH2:15][C:25]([O:29][CH2:30][CH3:31])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-O-benzyl-3-O-t-butyldimethylsilyl-2-O-mesylglycerol (0.83 g) was dissolved in N,N-dimethylformamide (5 ml), and ethyl thioglycolate (0.34 ml) and sodium ethoxide (sodium 0.07 g/ethanol 5 ml) were added thereto, and the mixture stirred at 80° C. for 6 hours. After removing the solvent by evaporation under reduced pressure, water was added to the residue and the solution was extracted with ethyl ether (20 ml×3).

Workup

customAfter removing the solvent
customby evaporation under reduced pressure, water
additionwas added to the residue
extractionthe solution was extracted with ethyl ether (20 ml×3)

Sources & evidence

ORD record: ord-a4e195e32b824beb826ae215217a2bab
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034087

Reaction notes

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