Thioglycerol → 6,7-Dihydroxy-2-methyl-4-thiaheptanoic acid t-butyl ester

HRID 1720801Notes

Reaction equation

HRID 1720801 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])[C:8]([CH3:10])=[CH2:9].C(N(CC)CC)C>O>[C:13]([O:12][C:7](=[O:11])[CH:8]([CH3:10])[CH2:9][S:1][CH2:2][CH:3]([OH:4])[CH2:5][OH:6])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 7291ThioglycerolHCID 8471TriethylamineHCID 11448tert-Butyl methacrylate

Product 1

HCID 106344486,7-Dihydroxy-2-methyl-4-thiaheptanoic acid t-butyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To thioglycerol (0.835 mI), t-butyl methacrylate (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 chloroform. 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 (2.11 g, yield 84%) as a colorless oily substance.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction mixture was extracted with chloroform
  3. washThe extract was washed with a 5% aqueous solution of citric acid
  4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-19c56e9a3c8349f9b565f6e2d1521d92
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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