Imidazole → 2-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-ethanol

HRID 470970Notes

Reaction equation

HRID 470970 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[C:9]1([CH2:18][CH2:19][OH:20])[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1.N1C=CN=C1>CN(C=O)C.C(OCC)(=O)C>[C:1]([Si:5]([CH3:8])([CH3:7])[O:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:18][CH2:19][OH:20])=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 50132051,4-Benzenediethanol

Product 1

HCID 233774542-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-ethanol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyldimethylchlorosilane (9.68 mL) was added to a solution of 2,2′-(1,4-phenylene)diethanol (example 5, step a) (8.64 g) and imidazole (10.21 g) in dry DMF (100 mL) cooled in an ice bath. After 45 min, the reaction mixture was diluted with ethyl acetate, washed three times with water and evaporated in vacuo. Purification was by silica gel chromatography, eluting with 5:1 isohexane:ethyl acetate to give the subtitled compound as a colourless oil. Yield 6.20 g.

Workup

  1. temperaturecooled in an ice bath
  2. washwashed three times with water
  3. customevaporated in vacuo
  4. customPurification
  5. washeluting with 5:1 isohexane

Sources & evidence

ORD record
ord-69d0d8f76f0d479eaf8468f1a800f345
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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