Thioglycerol → 6,7Dihydroxy-3methyl-4-thiaheptanoic acid t-butyl ester
Reaction equation
[SH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[C:7]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])/[CH:8]=[CH:9]/[CH3:10].C(N(CC)CC)C>O>[C:13]([O:12][C:7](=[O:11])[CH2:8][CH:9]([CH3:10])[S:1][CH2:2][CH:3]([OH:4])[CH2:5][OH:6])([CH3:16])([CH3:15])[CH3:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To thioglycerol (0.835 ml), t-butyl crotonate (10 ml) and triethylamine (1 ml) were added, followed by stirring at 60° C. for 48 hours. After cooling and addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with a 5% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled off, to yield the title compound (1.82 g, yield 73%) as a colorless oily substance.
Workup
- temperatureAfter cooling
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe extract was washed with a 5% aqueous solution of citric acid
- dry with materiala saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-8f641081fb3b4fbf8f3b3c0e8fc51e3e
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05506267
Reaction notes
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