Imidazole → HCID 11426411, compound

HRID 1872567Notes

Reaction equation

HRID 1872567 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:14]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])([CH3:16])[CH3:15].N1C=CN=C1.O>CN(C)C=O>[C:14]([Si:18]([CH3:20])([CH3:19])[O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 572437Ethyl (3-Hydroxyphenyl)acetate

Product 1

HCID 11426411HCID 11426411, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-hydroxyphenylacetate (6 g) and tertbutyldimethylsilyl chloride (6 g) in 80 ml of anhydrous dimethylformamide are added 5.66 g of imidazole and the mixture is stirred at room temperature for 1 hour 30 minutes. The reaction mixture is then poured into water and extracted twice with ethyl acetate. The pooled organic extracts are dried over sodium sulfate and concentrated to dryness to give 10 g of the product as a yellow oil.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe pooled organic extracts are dried over sodium sulfate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e7b4d40a02344960ad6cfcbf22c6d9f0
Source dataset
uspto-grants-2000_08
Patent number
US06110924

Reaction notes

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