Imidazole → HCID 10545487, compound

HRID 376386Notes

Reaction equation

HRID 376386 reaction equation
[C:1]([CH2:3][C:4]1[O:5][C:6](=[O:17])[C:7]2[C:13]([OH:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:8]=2[CH:9]=1)#[N:2].N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C1(C)C=CC=CC=1>CN(C)C=O>[Si:23]([O:14][C:13]1[C:7]2[C:6](=[O:17])[O:5][C:4]([CH2:3][C:1]#[N:2])=[CH:9][C:8]=2[CH:10]=[C:11]([O:15][CH3:16])[CH:12]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 1140TolueneHCID 28928tert-Butyldimethylsilyl chlorideHCID 10585588HCID 10585588, compound

Product 1

HCID 10545487HCID 10545487, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.70 g (11.68 mmol) of the 3-cyanomethyl-8-hydroxy-6-methoxy-1-oxo-1H-2-benzopyran obtained in Example 3 was suspended in 25 ml of dimethylformamide. 1.59 g (23.4 mmol) of imidazole and 2.82 g (18.7 mmol) of tert-butyldimethylsilyl chloride were successively added thereto under cooling with ice, and the resulting mixture was stirred for 2 hours. After completion of the reaction, the reaction mixture was mixed with toluene, washed once with 50 ml of a 10% aqueous solution of sodium chloride, and washed twice with 50 ml portions of a 20% aqueous solution of sodium chloride. The toluene layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and dried in vacuo. The resulting residue was recrystallized from 20 ml of ethanol to obtain 3.77 g of the title compound in a 93% yield.

Workup

  1. temperatureunder cooling with ice
  2. customAfter completion of the reaction
  3. washwashed once with 50 ml of a 10% aqueous solution of sodium chloride
  4. washwashed twice with 50 ml portions of a 20% aqueous solution of sodium chloride
  5. dry with materialThe toluene layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customdried in vacuo
  8. customThe resulting residue was recrystallized from 20 ml of ethanol

Sources & evidence

ORD record
ord-9dccdd351eab40c899e848a39e71f200
Source dataset
uspto-grants-2000_02
Patent number
US06020363

Reaction notes

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