Chlorotrimethylsilane → Trimethyl[(thiophen-2-yl)methyl]silane

HRID 1588370Notes

Reaction equation

HRID 1588370 reaction equation
[Li]CCCC.[C:6]1([S:12][CH3:13])[CH:11]=[CH:10]C=C[CH:7]=1.Cl[Si:15]([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[S:12]1[CH:13]=[CH:10][CH:11]=[C:6]1[CH2:7][Si:15]([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7520ThioanisoleHCID 178418339Butyllithium

Product 1

HCID 13547226Trimethyl[(thiophen-2-yl)methyl]silaneYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 143 mL of 1.4M n-BuLi (0.20 mol) in 55 mL of dry THF, was added dropwise at room temperature under a nitrogen atmosphere 24.8 g (0.20 mol) of thioanisole. Upon completion of the addition, the yellow mixture began to reflux spontaneously The mixture was stirred at room temperature for 3 hours. Upon addition of 21.84 g (0.20 mol) of chlorotrimethylsilane, the mixture again began to reflux spontaneously. After stirring at room temperature overnight, the mixture was quenched with 100 mL of 5% of HCl. The aqueous layer was separated, and the organic layer was dried over MgSO4, filtered, and the solvent removed in vacuo from a water bath at 45° C. The crude product was distilled to give 19.22 g (49%) of the colorless sulfide, bp 84°-86° C./0.3 Torr; 1H NMR (CDCL3) δ0.17 (s, 9H, Si(CH3)3), 2.13 (s, 2H, CH2S), 7.0-7.42 (m, 5H, phenyl).

Workup

  1. additionUpon completion of the addition
  2. temperatureto reflux spontaneously The mixture
  3. temperatureto reflux spontaneously
  4. stirringAfter stirring at room temperature overnight
  5. customthe mixture was quenched with 100 mL of 5% of HCl
  6. customThe aqueous layer was separated
  7. dry with materialthe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customthe solvent removed in vacuo from a water bath at 45° C
  10. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-4e9aaa429af047ef833a2d0b8054ee6e
Source dataset
uspto-grants-1993_06
Patent number
US05221754

Reaction notes

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