Dichlorodimethylsilane → HCID 18702790, compound

HRID 2287940Notes

Reaction equation

HRID 2287940 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[CH2:13][CH:12]=[CH:11]2.[CH3:19][Si:20]([CH3:23])(Cl)Cl>CCCCCC.C1COCC1>[CH3:19][Si:20]([CH3:23])([CH:13]1[C:14]2[C:10](=[CH:9][C:8]([O:7][CH3:6])=[C:16]([O:17][CH3:18])[CH:15]=2)[CH:11]=[CH:12]1)[CH:1]1[C:10]2[C:4](=[CH:15][C:16]([O:17][CH3:18])=[C:8]([O:7][CH3:6])[CH:9]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 600649HCID 600649, compoundHCID 178418339Butyllithium

Product 1

HCID 18702790HCID 18702790, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

23.6 ml (59 mmol) of a 2.5 M butyllithium solution in hexane were added at room temperature to a solution of 10.4 g (59 mmol) of 5,6-dimethoxyindene (prepared by the method of Eberson et al., Acta Chem. Scand. B 30 (1976) 527) in 150 ml of THF, and the mixture was stirred at room temperature for 2 hours and added dropwise to a solution of 3.6 ml (29.5 mmol) of dimethyldichlorosilane in 20 ml of THF. The mixture was stirred overnight, poured into ice water and extracted with ether. The extracts were dried using Na2SO4, and the solvent was stripped off. The residue was stirred with diethyl ether, 2.2 g (18%) of the ligand system crystallizing. 1H-NMR spectrum (CDCl3, 400 MHz): (2 diastereomers in the ratio 1:1) 6.82-6.87 (β-IndH), 6.55 (dd, α-IndH), 6.34 (dd, α-IndH), 3.91 (s, OCH3), 3.90 (s, OCH3), 3.87 (s, OCH3), 3.84 (s, OCH3), 3.53 (m, CH), 3.51 (m, CH), -0.05 (s, SiCH3), -0.24 (s, SiCH3), -0.41 (s, SiCH3). Mass spectrum: 408 M+, correct decomposition, correct isotope pattern.

Workup

  1. customprepared by the method of Eberson et al., Acta Chem
  2. extractionextracted with ether
  3. customThe extracts were dried
  4. stirringThe residue was stirred with diethyl ether, 2.2 g (18%) of the ligand system
  5. customcrystallizing

Sources & evidence

ORD record
ord-eb4e0c0ddde24a7cbdd64efec7231b09
Source dataset
uspto-grants-2000_07
Patent number
US06087292

Reaction notes

Loading…