Imidazole → (1,1-Dimethylethyl)[[2-[(hexadecyloxy)methyl]-2-propenyl]oxy]dimethylsilane

HRID 248144Notes

Reaction equation

HRID 248144 reaction equation
[CH2:1]([O:17][CH2:18][C:19](=[CH2:22])[CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].N1C=CN=C1>CN(C)C=O.CCOCC>[CH3:27][C:26]([Si:23]([O:21][CH2:20][C:19]([CH2:18][O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH2:22])([CH3:25])[CH3:24])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 113588863-Hexadecyloxy-2-methylenepropan-1-ol

Product 1

HCID 19764328(1,1-Dimethylethyl)[[2-[(hexadecyloxy)methyl]-2-propenyl]oxy]dimethylsilaneYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.0 g of 2-[(hexadecyloxy)-methyl]-2-propen-1-ol in 50 ml of dry N,N-dimethylformamide is added 6.05 g of tert-butyldimethylsilyl chloride followed by 8 g of imidazole. This mixture is stirred overnight, then diluted with ether, washed with saturated aqueous sodium bicarbonate, water and brine, dried and evaporated, to give 6.49 g of the desired compound.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate, water and brine
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-bdcc4d07a4b445ecabd7f80672461b4c
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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