Imidazole → HCID 11426411, compound

HRID 993065Notes

Reaction equation

HRID 993065 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-eee1656daf9341cabb8856876a3add9b
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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