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

HRID 1791970Notes

Reaction equation

HRID 1791970 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].C(N(CC)CC)C.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20].O>CN(C=O)C>[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:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 158291994-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-oneYield 82.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-1-indanone (25.0 g, 169 mmol) in DMF (500 ml) was triethylamine (22.2 g, 220 mmol) added, to the resulting solution was tert-butyldimethylchlorosilane (28.0 g, 186 mmol) added. 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 the indanone (36.68 g, 140 mmol, 82.7%) as a colourless oil (120–121° C./0.1 mbar).

Workup

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

Sources & evidence

ORD record
ord-d3f367f672ce48239ecf93d61c972ddf
Source dataset
uspto-grants-2006_07
Patent number
US07074863B2

Reaction notes

Loading…