Imidazole → Methyl 3-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]phenylacetate

HRID 278480Notes

Reaction equation

HRID 278480 reaction equation
[OH:1][CH2:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:10][CH:11]=1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C>[Si:23]([O:1][CH2:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:10][CH:11]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22628477Methyl 3-(4-hydroxy-3-oxobutyl)phenylacetate

Product 1

HCID 22628459Methyl 3-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]phenylacetateYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice cooled solution of methyl 3-(4-hydroxy-3-oxo-butyl)phenylacetate (472 mg, 2.00 mmol) in DMF (10 ml) was added imidazole (264 mg, 3.88 mmol) followed by tert-butyldimethylsilyl chloride (408 mg, 5.99 mmol). After 30 minutes the ice-bath was removed and then the mixture was stirred overnight at room temperature. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate), and concentrated in vacuo. The residue was purified by silica gel (20 g) column chromatography eluting with hexane/ethyl acetate (10:1) to give methyl 3-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]phenylacetate (664 mg, 94.9%) as a colorless oil.

Workup

  1. customAfter 30 minutes the ice-bath was removed
  2. additionThe reaction mixture was poured into water (100 ml)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel (20 g) column chromatography
  8. washeluting with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-b774a9a2e1924066b5eae6f3b0d8fa73
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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