Methanol → Chloromethyl(methoxy)methyl(phenyl)silane

HRID 1980511

Reaction equation

HRID 1980511 reaction equation
[CH3:1][OH:2].C(N(CC)CC)C.Cl[Si:11]([CH2:19][Cl:20])([CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOCC>[Cl:20][CH2:19][Si:11]([O:2][CH3:1])([CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 12418873Chloro(chloromethyl)methyl(phenyl)silane

Product 1

HCID 13474594Chloromethyl(methoxy)methyl(phenyl)silaneYield 79.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.6 ml (1.3 g, 0.040 mol) of methanol and 3.0 ml (2.2 g, 0.022 mol) of triethylamine in 100 ml of ether was stirred while a solution of 4.1 g (0.020 mol) of chloro(chloromethyl)methyl(phenyl)silane in 10 ml of ether was added dropwise. The resulting slurry was refluxed for 2 hours, cooled, washed with water, 0.1N aqueous HCl, saturated aqueous NaHCO3, water, and brine, dried over magnesium sulfate, and evaporated to leave 3.2 g of a pale yellow liquid. Distillation provided 1.7 g (42%) of the title compound as a colorless liquid: bp 46°-49° (0.05 mm); nD22 1.5207; nmr (CDCl3): 0.5 (3H, s), 3.0 (2H, s), 3.5 (3H, s) and 7.3-7.8 (5H, m).

Workup

  1. additionwas added dropwise
  2. temperatureThe resulting slurry was refluxed for 2 hours
  3. temperaturecooled
  4. washwashed with water, 0.1N aqueous HCl, saturated aqueous NaHCO3, water, and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-ccbcc20f7a204cd6b8dde25f043f5748
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Linked notes

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