Imidazole → 4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-benzoic acid ethyl ester

HRID 409324Notes

Reaction equation

HRID 409324 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[CH3:12])[CH3:2].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:7][C:6]=1[CH3:12])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 13356900Ethyl 4-hydroxy-2-methylbenzoate

Product 1

HCID 671102614-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-benzoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 18 g (100 mmol) of 4-hydroxy-2-methyl-benzoic acid ethyl ester (prepared according to Sen, et. al. (1987), Indian J. Chem. Sec B, 26: 679-682), 10.2 g (150 mmol) of imidazole, and 17.2 g (115 mmol) of tert-butyldimethylsilyl chloride in 110 mL of anhydrous DMF was stirred for 24 hours at room temperature. The reaction was diluted with water and extracted with ethyl acetate. The organic fraction was washed with water, 0.1 N HCl, and brine, then dried over anhydrous magnesium sulfate and concentrated to 28.8 g of the title compound; MS (ESI+): m/z 295.5 (M+1)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic fraction was washed with water, 0.1 N HCl, and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated to 28.8 g of the title compound

Sources & evidence

ORD record
ord-ed3d1541787b43478c5823af4246013c
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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