Imidazole → HCID 22345525, compound

HRID 1700943Notes

Reaction equation

HRID 1700943 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.N1C=CN=C1.[C:17]([Si:21](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 824523-(4-Hydroxyphenyl)propanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 22345525HCID 22345525, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 3-(4-hydroxyphenyl)-1-propanol (10.0 g, 66.0 mmol) and imidazole (6.7 g, 98.4 mmol) in N,N-dimethylformamide (50 ml) was cooled to 0-5° C. and treated dropwise with tert-butylchlorodiphenylsilane (21.5 g, 78.2 mmol). The resulting mixture was stirred at 0-5° C. for 2 h and then quenched by addition of water (400 ml) and toluene (500 ml). The organic phase was washed with water, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and chromatography of the residue or silica gel (elution toluene-ethyl acetate, 95:5) gave 24.8 g (96%) of the title material as a clear oil.

Workup

  1. customquenched by addition of water (400 ml) and toluene (500 ml)
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent and chromatography of the residue or silica gel (elution toluene-ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-1b1bdac49721433ea4d51a7a89647275
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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