Imidazole → Methyl (R)-2-[(tert-butyldimethylsilyl)oxy]-2-(3-chlorophenyl)acetate

HRID 1004072Notes

Reaction equation

HRID 1004072 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)[OH:5].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)[O:5][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 15606324(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

Product 1

HCID 54113343Methyl (R)-2-[(tert-butyldimethylsilyl)oxy]-2-(3-chlorophenyl)acetateYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-(3-chloro-phenyl)-hydroxy-acetic acid methyl ester (21.0 g), imidazole (14.25 g), and tert-butyidimethylsilyl chloride (25.0 g) in N,N-dimethylformamide (250 ml) was stirred at room temperature for 18 h. The mixture was poured into water (2.5 l) and extracted with ethyl acetate. The combined extracts were washed with water and saturated brine, dried, and concentrated. The residue was purified by flash chromatography, eluting with cyclohexane:ethyl acetate (9:1) to give the title compound as a colourless oil (32.63 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water and saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with cyclohexane:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-1e40d8fb457b4292897a4778971e3266
Source dataset
uspto-grants-2000_04
Patent number
US06048872

Reaction notes

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