Imidazole → 4-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-one

HRID 1253799Notes

Reaction equation

HRID 1253799 reaction equation
[OH:1][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.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C(OCC)(=O)C>CN(C)C=O>[O:1]([C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11])[Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 158291994-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-dihydro-4-hydroxy-1H-inden-1-one (1.0 g) in N,N-dimethylformamide (10 mL), imidazole (1.01 g) and tert-butyldimethylsilyl chloride (1.32 g) were sequentially added and the resultant reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into ethyl acetate-saturated aqueous sodium bicarbonate and the resultant reaction mixture was subjected to a phase separation. The organic phase was washed sequentially with water and a saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate: n-hexane:ethyl acetate=95:5 to 90:10) to obtain the subject compound (1.63 g) as a pale yellow oil.

Workup

  1. customthe resultant reaction mixture
  2. customthe resultant reaction mixture
  3. customwas subjected to a phase separation
  4. washThe organic phase was washed sequentially with water
  5. dry with materiala saturated saline and was dried over anhydrous sodium sulfate
  6. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
  7. customthe resultant residue was purified by silica gel column chromatography (eluate: n-hexane:ethyl acetate=95:5 to 90:10)

Sources & evidence

ORD record
ord-1db0adb35afe46798c637f9c0d492fb8
Source dataset
uspto-grants-2013_06
Patent number
US08455500B2

Reaction notes

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