Dichlorodimethylsilane → HCID 21188885, compound

HRID 356830Notes

Reaction equation

HRID 356830 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.[CH3:21][Si:22]([CH3:25])(Cl)Cl>C1(C)C=CC=CC=1.O=O>[CH3:21][Si:22]([CH3:25])([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 3

HCID 6398DichlorodimethylsilaneHCID 129423867-Phenyl-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 21188885HCID 21188885, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 977OxygenSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

18.7 cm3 (50 mmol) of a 20 % strength solution of butyl-lithium in toluene were added at room temperature to a solution of 10 g (50 mmol) of 10 in 100 cm3 of H2O- 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-dd5c94cb50e64477809b8ff450b65e76
Source dataset
uspto-grants-1998_11
Patent number
US05840644

Reaction notes

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