Imidazole → HCID 68957642, compound

HRID 2378069Notes

Reaction equation

HRID 2378069 reaction equation
N1C=CN=C1.[CH3:6][O:7][C:8]([C:10]1([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[C:14]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:12][CH2:11]1)=[O:9].[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>C1COCC1.[Cl-].[Na+].O>[CH3:6][O:7][C:8]([C:10]1([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])=[CH:20][CH:19]=3)[C:14]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:11][CH2:12]1)=[O:9]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 136395593HCID 136395593, compound

Product 1

HCID 68957642HCID 68957642, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Imidazole (2.1 g) is added to a solution consisting of the 1-[3-(4-hydroxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropanecarboxylic acid methyl ester (9.6 g) and tert-butyldimethylsilyl chloride (4.7 g) in THF (100 mL). The reaction mixture is stirred at room temperature overnight. Brine solution is added and the reaction mixture is twice extracted with ethyl acetate. The combined extracts are dried and concentrated. Repeated concentration from hexane and then pentane gave 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropanecarboxylic acid methyl ester (12.8 g.)

Workup

  1. extractionthe reaction mixture is twice extracted with ethyl acetate
  2. customThe combined extracts are dried
  3. concentrationconcentrated
  4. concentrationconcentration from hexane

Sources & evidence

ORD record
ord-c8685dd35471478789b8de2d53cd3581
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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