Imidazole → HCID 22033913, compound

HRID 1791969Notes

Reaction equation

HRID 1791969 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.N1C=CN=C1.[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19].O>CN(C=O)C>[O:1]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2)[Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 21828375HCID 21828375, compound

Product 1

HCID 22033913HCID 22033913, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 7-hydroxy-2-methyl-1-indanone (6) (10.2 g, 37 mmol) and imidazole (3.02 g, 44 mmol) dissolved in DMF (200 ml) was added tert-butyldimethylchlorosilane (6.11 g, 41 mmol) in DMF (50 ml). The reaction mixture was stirred overnight at room temperature and treated with water (200 ml) and extracted with diethylether (2×200 ml). The combined organic phases were washed with aqueos NH4Cl (300 ml), brine (100 ml) and dried over sodium sulfate. Evaporation gave (7) as a yellow oil which was used without further purification.

Workup

  1. extractionextracted with diethylether (2×200 ml)
  2. washThe combined organic phases were washed with aqueos NH4Cl (300 ml), brine (100 ml)
  3. dry with materialdried over sodium sulfate
  4. customEvaporation

Sources & evidence

ORD record
ord-954144c60d7e4434824a463f16a0b3ac
Source dataset
uspto-grants-2006_07
Patent number
US07074863B2

Reaction notes

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