Pyridine → HCID 44439004, compound

HRID 556713Notes

Reaction equation

HRID 556713 reaction equation
COC1C=CC([CH:9]2O[CH:10]2[C:12]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[O:13])=CC=1.B(F)(F)F.C[CH2:31][O:32][CH2:33][CH3:34].Cl.[NH2:36]O.N1C=[CH:42][CH:41]=[CH:40][CH:39]=1>CCOCC>[CH3:31][O:32][C:33]1[CH:34]=[CH:42][C:41]([C:10]2[CH:9]=[N:36][O:13][C:12]=2[C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8000Boron trifluoride etherateHCID 443297Hydroxyamine hydrochlorideHCID 11371341[3-(4-methoxy-phenyl)-oxiranyl]-(3,4,5-trimethoxy-phenyl)-methanone

Product 1

HCID 44439004HCID 44439004, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of [3-(4-methoxy-phenyl)-oxiranyl]-(3,4,5-trimethoxy-phenyl)-methanone (0.5 g, 1.45 mmol) in dry ether (15 mL) was added BF3.Et2O (2.52 mL) slowly. After the addition, it was heated to reflux for 1 h. After the reaction mixture had cooled to room temperature, it was poured into ice-H2O (100 mL). The etheral layer was separated and the aqueous layer was extracted with ether (10 mL×3). The combined ether layers were washed with H2O (20 mL×2) and concentrated to dryness. The residue was then transferred with EtOH (3 mL) to a flask suited for a microwave reactor, and hydroxylamine hydrochloride (0.32 g, 4.6 mmol) and pyridine (1 mL) were added. The mixture was heated and stirred in a microwave reactor at 130° C. for 30 min. The reaction mixture was then cooled to room temperature and poured into ice-H2O (20 mL). The solid material was collected and washed with H2O. After preparative HPLC or repeated solvating gas chromatography (SGC) (hexane to 14% Hexane/EtOAc), the product 4-(4-Methoxy-phenyl)-5-(3,4,5-trimethoxy-phenyl)-isoxazole was obtained as a light yellow solid. 1H-NMR (CDCl3) δ 3.70 (s, 6H), 3.82 (s, 3H), 3.85 (s, 3H), 6.85 (s, 2H), 6.94 (d, 2H, J=8), 7.33 (d, 2H, J=8), 8.30 (s, 1H) ppm; ESMS calcd for C19H19NO5: 341.0. Found: 342.0 (M+H+).

Workup

  1. additionAfter the addition, it
  2. temperaturewas heated
  3. temperatureto reflux for 1 h
  4. customThe etheral layer was separated
  5. extractionthe aqueous layer was extracted with ether (10 mL×3)
  6. washThe combined ether layers were washed with H2O (20 mL×2)
  7. concentrationconcentrated to dryness
  8. customThe residue was then transferred with EtOH (3 mL) to a flask
  9. customsuited for a microwave reactor
  10. temperatureThe mixture was heated
  11. temperatureThe reaction mixture was then cooled to room temperature
  12. customThe solid material was collected
  13. washwashed with H2O

Sources & evidence

ORD record
ord-c3b465fc040f4e8e9ca531f949cbba64
Source dataset
uspto-grants-2011_11
Patent number
US08058297B2

Reaction notes

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