Imidazole → HCID 22345525, compound

HRID 584145Notes

Reaction equation

HRID 584145 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 hours 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 on 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 on silica gel (elution toluene-ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-328cd7fb98ca4a0ebbbf2d701db59bd4
Source dataset
uspto-grants-2005_08
Patent number
US06924391B2

Reaction notes

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