Imidazole → HCID 14626270, compound

HRID 477783Notes

Reaction equation

HRID 477783 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[C:4]=2[CH:3]=1.N1C=CN=C1.[C:23]([Si:27]([CH3:30])([CH3:29])Cl)([CH3:26])([CH3:25])[CH3:24].C1(C)C=CC=CC=1>CN(C)C=O>[CH3:29][Si:27]([CH3:30])([C:23]([CH3:26])([CH3:25])[CH3:24])[O:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 1140TolueneHCID 28928tert-Butyldimethylsilyl chlorideHCID 677495HCID 677495, compound

Product 1

HCID 14626270HCID 14626270, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10 g of 2-hydroxy-6,11-dihydrodibenz[b,e]oxepin-11-one in 50 ml of dimethylformamide are added 6.5 g of imidazole and 7 g of t-butyldimethylchlorosilane and the mixture is stirred for 1 hour. After adding 300 ml of toluene, successively washing with water and a saturated saline solution and drying over magnesium sulfate, the solvent is distilled off under reduced pressure to give 13 g of 2-(dimethyl-t-butylsilyloxy)-6,11-dihydrodibenz[b,e]oxepin-11-one (oil). Mass spectrum m/z: 340(M+).

Workup

  1. washsuccessively washing with water
  2. dry with materiala saturated saline solution and drying over magnesium sulfate
  3. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-bd69a7a676184ed994a6a2f6fee5647f
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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