Imidazole → Methyl (3S)-3-(tert-butyldiphenylsilyloxy)-butyrate

HRID 1623564Notes

Reaction equation

HRID 1623564 reaction equation
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][O:20][C:21](=[O:26])[CH2:22][C@@H:23]([OH:25])[CH3:24].N1C=CN=C1>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[CH3:19][O:20][C:21](=[O:26])[CH2:22][C@@H:23]([O:25][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:24]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 6950307Methyl 3-hydroxybutyrate, (S)-

Product 1

HCID 68783265Methyl (3S)-3-(tert-butyldiphenylsilyloxy)-butyrate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl(chloro)diphenylsilane (15.282 g, 55.6 mmol) was added dropwise to an ice-cooled and stirred solution of (S)-3-hydroxybutanoic acid methyl ester (5.473 g, 46.3 mmol) and 1H-imidazole (6.939 g, 102 mmol) and DMAP (0.566 g, 4.63 mmol) in DMF (250 mL). After 10 min., the cloudy reaction mixture was allowed to warm to r.t. and stirred overnight. The reaction mixture was taken up in EtOAc, then washed successively with H2O (3×), 1N HCl and a sat. NaHCO3 solution. The organic phase was dried (Na2SO4), filtered and concentrated to give a viscous colourless oil.

Workup

  1. temperaturecooled
  2. customthe cloudy reaction mixture
  3. washwashed successively with H2O (3×), 1N HCl
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a viscous colourless oil

Sources & evidence

ORD record
ord-9c7ec4b4c3fe46e9b098b246f50b2073
Source dataset
uspto-grants-2014_07
Patent number
US08778974B2

Reaction notes

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