Imidazole → 1-Indanone

HRID 1791968Notes

Reaction equation

HRID 1791968 reaction equation
O[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].N1C=CN=C1.C([Si](C)(C)Cl)(C)(C)C.O>CN(C=O)C>[CH2:4]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][CH:2]=2)[C:6](=[O:11])[CH2:5]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 67351-IndanoneYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-1-indanone (25.0 g, 169 mmol) and imidazole (28.7 g, 422 mmol) in DMF (500 ml) was added tert-butyldimethylchiorosilane. The reaction mixture was stirred overnight at room temperature and treated with water (500 ml) and extracted with diethyl ether (500 ml). The organic phase was collected and dried over sodium sulfate. Evaporation gave a yellow oil which was distilled under reduced pressure to give indanone (1) (35.44 g, 135 mmol, 79.9%) as a colourless oil (120–121° C./0.1 mbar).

Workup

  1. extractionextracted with diethyl ether (500 ml)
  2. customThe organic phase was collected
  3. dry with materialdried over sodium sulfate
  4. customEvaporation
  5. customgave a yellow oil which
  6. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-c27413ba3f90416cbba4e2a1548bf543
Source dataset
uspto-grants-2006_07
Patent number
US07074863B2

Reaction notes

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