Ethyl Acetate → (Chloromethyl)(triphenyl)silane

HRID 1980508

Reaction equation

HRID 1980508 reaction equation
[Cl:1][CH2:2][Si:3](Cl)(Cl)Cl.[C:7]1([Li])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O[CH2:18][CH3:19])(=O)C>CCOCC>[Cl:1][CH2:2][Si:3]([C:19]1[CH:18]=[CH:9][CH:8]=[CH:7][CH:12]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 15258Trichloro(chloromethyl)silaneHCID 178506676HCID 178506676, compound

Product 1

HCID 261116(Chloromethyl)(triphenyl)silane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 12.6 ml (18.4 g, 0.10 mol) of (chloromethyl)trichlorosilane in 150 ml of dry ether was stirred under nitrogen and chilled in ice while 162 ml (0.30 mol) of 1.85 molar phenyllithium in cyclohexane-ether 70:30 was added dropwise at a rate that held the mixture below 15° C. The resulting slurry was stirred overnight at room temperature, treated carefully with 10 ml of ethyl acetate to quench any remaining phenyllithium, washed with water and brine, dried over magnesium sulfate, and evaporated to leave 33 g of sticky solid. Recrystallization from 30 ml of cyclohexane provided 15.8 g (51%) of the title compound as an off white solid: m.p. 112°-115° C.; ir (Nujol®) 1420, 1110, 735, 730, 705, 695 cm-1 ; nmr (CDCl3) 3.5 (2H, s), 7.0-7.8 (15H, m).

Workup

  1. additionwas added dropwise at a rate that
  2. customthe mixture below 15° C
  3. customto quench any remaining phenyllithium
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-4ebcbc91dd45421ab94367c53b75cbf1
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Linked notes

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