Chlorotrimethylsilane → 2-trimethylsilyloxy-1H-indene

HRID 2380218Notes

Reaction equation

HRID 2380218 reaction equation
C(N(CC)CC)C.[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C:9]1=[O:17].[CH3:18][Si:19]([CH3:22])([CH3:21])Cl>O1CCCC1>[CH3:18][Si:19]([CH3:22])([CH3:21])[O:17][C:9]1[CH2:10][C:11]2[C:16]([CH:8]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 119832-Indanone

Product 1

HCID 108997362-trimethylsilyloxy-1H-indeneYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl alpha-2-[2'-(3"-cyclopropylisoxazol-5"-yl)-ethen-1'-yl]-phenyl-β-methoxyacrylate ##STR10## a) 30.3 g (0.30 mole) of triethylamine are added to a solution of 36.5 g (0.28 mole) of 2-indanone and 32.4 g (0.30 mole) of trimethylchlorosilane in 300 ml of tetrahydrofuran at room temperature while stirring. Stirring is continued for a further 3 hours at room temperature (20° C.), the precipitate which has separated out is filtered off under suction and the filtrate is evaporated down. The residue is purified by distillation (53° C., 0.3 mbar). 40.6 g (72%) of 2-trimethylsilyloxy-1H-indene are obtained as a colorless liquid in this manner.

Workup

  1. stirringStirring
  2. custom(20° C.), the precipitate which has separated out
  3. filtrationis filtered off under suction
  4. customthe filtrate is evaporated down
  5. distillationThe residue is purified by distillation (53° C., 0.3 mbar)

Sources & evidence

ORD record
ord-c883c5bb37fa47fd9c53c967507e7a1c
Source dataset
uspto-grants-1994_11
Patent number
US05366984

Reaction notes

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