Oxygen → HCID 21188885, compound

HRID 1066379Notes

Reaction equation

HRID 1066379 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[C:6]1([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:20]=2[CH2:19][CH:18]=[CH:17]3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O=O.[CH3:23][Si:24]([CH3:27])(Cl)Cl>C1(C)C=CC=CC=1>[CH3:23][Si:24]([CH3:27])([CH:17]1[C:16]2[C:20](=[C:12]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:13]=[CH:14][CH:15]=2)[CH:19]=[CH:18]1)[CH:1]1[C:17]2[C:4](=[C:12]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:20]=[CH:19][CH:18]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 977Oxygen2×HCID 6398DichlorodimethylsilaneHCID 129423867-Phenyl-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 21188885HCID 21188885, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

18.7 cm3 (50 mmol) of a 20% strength solution of butyllithium in toluene were added at room temperature to a solution of 10 g (50 mmol) of 10 in 100 cm3 of H2)- and O2-free toluene and 5 ml of H2O- and O2-free THF, and the mixture was heated at 80° C. for 2 hours. The yellow suspension was subsequently cooled to 0° C. and 3.2 g (25 mmol) of dimethyldichlorosilane were added. The reaction mixture was heated at 80° C. for a further 1 hour and subsequently washed with 50 cm3 of H2O. The solvent was removed in vacuo, and the residue was recrystallized from heptane at −20° C. giving 6.7 g (62%) of 11 as colorless crystals (m.p. 109-110° C.).

Workup

  1. temperatureThe yellow suspension was subsequently cooled to 0° C.
  2. temperatureThe reaction mixture was heated at 80° C. for a further 1 hour
  3. washsubsequently washed with 50 cm3 of H2O
  4. customThe solvent was removed in vacuo
  5. customthe residue was recrystallized from heptane at −20° C.

Sources & evidence

ORD record
ord-4f491f5f85ca49d9a63aaa0632259ef7
Source dataset
uspto-grants-2001_06
Patent number
US06242544B1

Reaction notes

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