Water → (1,1-Dimethylethoxy)(1H-imidazol-1-ylmethyl)methyl(phenyl)silane

HRID 2413311Notes

Reaction equation

HRID 2413311 reaction equation
Cl[CH2:2][Si:3]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Na].[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.O>CN(C)C=O>[CH3:13][C:12]([CH3:15])([O:11][Si:3]([CH2:2][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)([CH3:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 13474595Chloromethyl(1,1-dimethylethoxy)methyl(phenyl)silaneHCID 57373095Imidazole sodium

Product 1

HCID 54326790(1,1-Dimethylethoxy)(1H-imidazol-1-ylmethyl)methyl(phenyl)silaneYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.6 g (0.015 mol) of chloromethyl(1,1-dimethylethoxy)methyl(phenyl)silane and 1.3 g (0.015 mol) of imidazole sodium salt in 10 ml of dimethylformamide was stirred at 50° for 3 hours, allowed to stand at room temperature for 72 hours, poured into water, and extracted with ether. The ether extracts were washed three times with water and once with brine, dried over magnesium sulfate, and evaporated to leave 3.8 g of an oil. Impurities were removed by Kugelrohr distillation at 90° (airbath)/0.05 mm to leave 2.9 g (71%) of the title compound as a pale yellow oil: nD20 15291; ir (neat) 3105, 3070, 3045, 2970, 1590, 1500, 1425, 1360, 1250, 1235, 1185, 1110, 1055, 1020, 900, 805, 740, 700, 660 cm-1 ; nmr (CDCl3): 0.6 (3H, s), 1.3 (9H, s), 3.6 (2H, s), 6.8 (1H, s), 7.0 (1H, s) and 7.3-7.7 (6H, m).

Workup

  1. waitto stand at room temperature for 72 hours
  2. extractionextracted with ether
  3. washThe ether extracts were washed three times with water
  4. dry with materialonce with brine, dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-0e74463d898246e5b0a411f92dbb1b83
Source dataset
uspto-grants-1985_01
Patent number
US04496551

Reaction notes

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