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

HRID 481707Notes

Reaction equation

HRID 481707 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 (3×). The combined ether extracts were washed with water (2×), 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 colourless oil (14.12 g) in 88% yield. 1H NMR (300MHz, CDCl3) d: 1.08 (s, 9H, t-butyl), 1.39 (t, 1H, J=9 Hz, SH), 1.95 (bs, 1H, OH), 2.68 (dd, 2H, J=9 Hz, 5.5Hz, H-3), 3.72 (m, 3H, H-1 and H-2), 7.43 and 7.66 (m, 10H, Ar-H).

Workup

  1. customwas quenched by the addition of saturated sodium bicarbonate
  2. extractionthe mixture was extracted with ether (3×)
  3. washThe combined ether extracts were washed with water (2×), 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-15b5e4d0520f48afa34e1ca1042e78e0
Source dataset
uspto-grants-1998_08
Patent number
US05789394

Reaction notes

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