Imidazole → 1-t-BUTYLDIPHENYLSILYLOXY-3-MERCAPTO-2-PROPANOL

HRID 365766Notes

Reaction equation

HRID 365766 reaction equation
[SH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].N1C=CN=C1.[Si:12](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[Si:12]([O:5][CH2:4][CH:3]([OH:6])[CH2:2][SH:1])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 7291ThioglycerolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 212558771-t-BUTYLDIPHENYLSILYLOXY-3-MERCAPTO-2-PROPANOLYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-mercapto-1,2-propanediol (5.00 g, 46.23 mmol) and imidazole (3.78 g, 55.47 mmol) in dimethylformamide (30 mL) was added t-butyldiphenylsilyl chloride (12.71 g, 46.23 mmol) at room temperature. After stirring for 18 h the reaction was quenched by the addition of saturated sodium bicarbonate and the mixture was extracted with ether (3X). The combined ether extracts were washed with water (2X), brine, dried and concentrated to give a yellow oil. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (90:10) to give the compound as a colorless oil (14.12 g) in 88% yield.

Workup

  1. customwas quenched by the addition of saturated sodium bicarbonate
  2. extractionthe mixture was extracted with ether (3X)
  3. washThe combined ether extracts were washed with water (2X), brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customThe crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (90:10)

Sources & evidence

ORD record
ord-9ce6b254777b40349633a61135b58196
Source dataset
uspto-grants-2000_10
Patent number
US06127540

Reaction notes

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