Imidazole → Methyl 2-(4-tert-butyldimethylsilyloxymethyl-2-propylphenoxy)-2-phenylacetate

HRID 1492629Notes

Reaction equation

HRID 1492629 reaction equation
[OH:1][CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH2:21][CH2:22][CH3:23])[CH:4]=1.N1C=CN=C1.[C:29]([Si:33]([CH3:36])([CH3:35])Cl)([CH3:32])([CH3:31])[CH3:30].C(OCC)(=O)C>CN(C=O)C>[Si:33]([O:1][CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH2:21][CH2:22][CH3:23])[CH:4]=1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 19802778Methyl (4-hydroxymethyl-2-propylphenoxy)-2-phenylacetate

Product 1

HCID 19385617Methyl 2-(4-tert-butyldimethylsilyloxymethyl-2-propylphenoxy)-2-phenylacetateYield 61.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.34 g (7.45 mmol) of the product of Step J in DMF (30 mL) were added imidazole (609 mg, 8.94 mmol) and tertbutyldimethyl-chlorosilane (1.35 g, 8.94 mmol) at 0° C. The solution was stirred at room temperature for 18 hours, and was then poured into 100 mL of ethyl acetate and washed with H2O (2×). The water layer was extracted with ethyl acetate (2×). The combined organic layer was washed with H2O (3×) and brine, and was dried over anhydrous MgSO4. After concentration the mixture was purified by flash chromatography (hexane: EtOAc=10:1) to give 1.96 g of the title compound as a clear oil.

Workup

  1. washwashed with H2O (2×)
  2. extractionThe water layer was extracted with ethyl acetate (2×)
  3. washThe combined organic layer was washed with H2O (3×) and brine
  4. dry with materialwas dried over anhydrous MgSO4
  5. concentrationAfter concentration the mixture
  6. customwas purified by flash chromatography (hexane: EtOAc=10:1)

Sources & evidence

ORD record
ord-0f1070698df14a9ebed76439f4200f2c
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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