Chlorotrimethylsilane → 1-Trimethylsiloxyindene

HRID 34263

Reaction equation

HRID 34263 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].C(N(CC)CC)C.[C:13]1(=[O:22])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1>CN(C)C=O.CCCCC>[CH3:1][Si:2]([CH3:4])([CH3:3])[O:22][CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 67351-IndanoneHCID 8471Triethylamine

Product 1

HCID 140001951-Trimethylsiloxyindene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8003PentaneSolvent

Procedure

Trimethylsilyl chloride (5.7 g, 52.3 mmole), triethylamine (11.71 g, 116 mmole), and 1-indanone (6.22 g, 47.1 mmole) were dissolved in dimethyl formamide (25 mL) and refluxed for 17 hours. After cooling, the mixture was diluted with pentane (50 mL) and washed four times with saturated sodium bicarbonate. After backwashing the aqueous phase with pentane the organic layers were combined, washed with cold 2N HCl and cold saturated sodium bicarbonate, then dried over MgSO4. The solvent was evaporated and the residue distilled (bp 123°-125° C.).

Workup

  1. temperaturerefluxed for 17 hours
  2. temperatureAfter cooling
  3. washwashed four times with saturated sodium bicarbonate
  4. washwashed with cold 2N HCl and cold saturated sodium bicarbonate
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated
  7. distillationthe residue distilled (bp 123°-125° C.)

Sources & evidence

ORD record
ord-4d1857117c354952a4bf1552ec242980
Source dataset
uspto-grants-1988_08
Patent number
US04761403

Linked notes

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