Ethyl Acetate → HCID 13392403, compound

HRID 1980515Notes

Reaction equation

HRID 1980515 reaction equation
[Cl:1][CH2:2][SiH2:3][CH:4](OCC)OCC.[C:11]1([Li])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:18](OCC)(=[O:20])[CH3:19]>CCOCC>[Cl:1][CH2:2][Si:3]([O:20][CH2:18][CH3:19])([CH3:4])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 91996060HCID 91996060, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 13392403HCID 13392403, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 18.2 ml (18.2 g, 0.10 mol) of chloromethyl(diethoxy)methylsilane in 200 ml of dry ether was stirred vigorously under N2 and chilled while 56 ml (0.10 mol) of 1.8 molar phenyllithium in 70:30 cyclohexane-ether was added at a rate that held the mixture below -50°. The resulting slurry was allowed to warm to room temperature, treated cautiously with 10 ml of ethyl acetate, washed with water and brine, dried over magnesium sulfate, and evaporated to leave 16.8 g of a golden yellow liquid. Distillation provided 9.5 g (44%) of the title compound as a colorless liquid: bp 80°-84° (0.1 mm); nD20 1.5144; nmr (CDCl3) 0.5 (3H, s), 1.2 (3H, t, J=7), 3.0 (2H, s), 3.8 (2H, q, J=7), 7.2-7.8 (5H, m).

Workup

  1. additionwas added at a rate that
  2. customthe mixture below -50°
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d25c939d2fa547d78524e326183ccd1e
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

Loading…