Potassium Carbonate → HCID 59264710, compound

HRID 2097277Notes

Reaction equation

HRID 2097277 reaction equation
B(F)(F)F.C[O+](C)C.[CH2:9]([O:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]([Br:31])=[CH:19][C:18]=1[C:32]1ON=[C:34]([CH3:37])[C:33]=1[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[NH2:47][OH:48].C(=O)([O-])[O-].[K+].[K+]>ClCCl.CO>[CH2:9]([O:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]([Br:31])=[CH:19][C:18]=1[C:32]1[C:33]([C:38]2[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)=[C:34]([CH3:37])[O:48][N:47]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 59264722HCID 59264722, compoundHCID 86608635HCID 86608635, compound

Product 1

HCID 59264710HCID 59264710, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Trimethyloxonium boron trifluoride (Aldrich; 70 mg, 0.47 mmol) was added to a stirred solution of 5-(2,4-Bis-benzyloxy-5-bromo-phenyl)-4-(4-methoxy-phenyl)-3-methyl-isoxazole (Example 3, Step 1) (120 mg, 0.22 mmol) in dichloromethane (3 ml) and stirring was continued for 3 h. The resulting mixture was concentrated in vacuo to leave a white semisolid, which was mixed with hydroxylamine hydrochloride (70 mg, 1.0 mmol), potassium carbonate (120 mg, 0.87 mmol) and methanol (2 ml), and heated at reflux for 18 h. The reaction mixture was partitioned between water (20 ml) and ethyl acetate (2×10 ml) and the combined organic phases were dried over anhydrous magnesium sulphate and evaporated in vacuo to leave an colourless oil. The crude product was purified by column chromatography, silica (10 g), eluting with hexane, followed by diethyl ether/hexane (1:1), to give 3-(2,4-Bis-benzyloxy-5-bromo-phenyl)-4-(4-methoxy-phenyl)-5-methyl-isoxazole as a white solid (44 mg, 37%)

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customto leave a white semisolid, which
  3. temperatureheated
  4. temperatureat reflux for 18 h
  5. customThe reaction mixture was partitioned between water (20 ml) and ethyl acetate (2×10 ml)
  6. dry with materialthe combined organic phases were dried over anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. customto leave an colourless oil
  9. customThe crude product was purified by column chromatography, silica (10 g)
  10. washeluting with hexane

Sources & evidence

ORD record
ord-f506b72a281d4bb78ad09a5c6f737825
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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