Potassium Carbonate → HCID 178519913, compound

HRID 455955Notes

Reaction equation

HRID 455955 reaction equation
[CH:1]1([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:22]=[CH:21][O:20][N:19]=4)=[CH:14][CH:13]=3)[C:10](=[O:23])[C:9]([OH:24])=[C:8]2[C:25](=[O:34])[C:26]2[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>ClCCl>[CH:1]1([CH:7]2[N:11]([C:12]3[CH:13]=[CH:14][C:15]([C:18]4[CH:22]=[CH:21][O:20][N:19]=4)=[CH:16][CH:17]=3)[C:10](=[O:23])[C:9]([OH:24])=[C:8]2[C:25](=[O:34])[C:26]2[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 25134Boron tribromide2×HCID 178491318HCID 178491318, compound

Product 1

HCID 178519913HCID 178519913, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 5-cyclohexyl-3-hydroxy-1-(4-isoxazol-3-ylphenyl)-4-(4-methoxybenzoyl)-1,5-dihydropyrrol-2-one (0.229 g, 0.5 mmol) and dichloromethane (10 mL), 1M boron tribromide in dichloromethane (5.0 mL, 5 mmol) was added under ice-cooling conditions and the mixture was stirred at r.t. for 3 days. Small amount of potassium carbonate was added under ice-cooling conditions to degrade excess boron tribromide. 1N aqueous sodium hydroxide was added and the mixture was washed with ethyl acetate. The aqueous layer was neutralized with 1N hydrochloric acid, the precipitate was collected by filtration and washed with hot ethyl acetate to give 5-cyclohexyl-3-hydroxy-4-(4-hydroxybenzoyl)-1-(4-isoxazol-3-ylphenyl)-1,5-dihydropyrrol-2-one (0.068 g, 31%) as colorless crystals.

Workup

  1. additionwas added under ice-
  2. temperaturecooling conditions
  3. temperaturecooling conditions
  4. washthe mixture was washed with ethyl acetate
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with hot ethyl acetate

Sources & evidence

ORD record
ord-dde7d52995ee4491a8476690304db120
Source dataset
uspto-grants-2013_07
Patent number
US08497263B2

Reaction notes

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