Chlorotrimethylsilane → Benzhydryl(trimethyl)silane

HRID 1603426Notes

Reaction equation

HRID 1603426 reaction equation
[C:1]1([CH:7]([K])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[Si:16]([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:1]1([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 178506622HCID 178506622, compound

Product 1

HCID 239056Benzhydryl(trimethyl)silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.01 g (24.3 mmol) of diphenylmethyl potassium in 25 mL of THF was added about 10 mL (about 8.6 g, 80 mmol) of chlorotrimethylsilane. The dark orange color instantly faded. The solvent was removed under reduced pressure. The residue was extracted with hexane and filtered and the solvent was removed under pressure to give the product as a pale yellowish liquid. The yield was 4.63 g, 79.3 percent. 1H NMR (C6D6) δ 7.08-7.23 (m, 8H), 6.98-7.06 (m, 2H), 3.41 (s, 1H), 0.00 (s, 9H). 13C NMR (C6D6) δ 143.2, 129.1, 128.6, 125.4, 46.5, -1.4.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionThe residue was extracted with hexane
  3. filtrationfiltered
  4. customthe solvent was removed under pressure

Sources & evidence

ORD record
ord-c89b54dd2a24498fb567480030297aed
Source dataset
uspto-grants-1999_11
Patent number
US05990033

Reaction notes

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