Acetic Anhydride → 3-(4-Hydroxy-phenyl)-benzo[d]isoxazol-6-ol

HRID 1816406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816406
O[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[N:10][OH:11].C(OC(=O)C)(=O)C.CCN(CC)CC.O.[Cl-].[Na+].O>>[OH:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=3[O:11][N:10]=2)=[CH:2][CH:7]=1

Komponenten

5

Edukt 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23713072Sodium chloride dihydrateHCID 136342142(2,4-Dihydroxyphenyl)(4-hydroxyphenyl)methanone Oxime

Produkt 1

HCID 1355269583-(4-Hydroxy-phenyl)-benzo[d]isoxazol-6-olAusbeute 44,7 %

Versuchsvorschrift

A mixture of (2,4-dihydroxyphenyl)(4-hydroxyphenyl)methanone oxime (0.46 g, 1.87 mmol), acetic anhydride (0.19 g, 1.87 mmol) and Et3N (0.25 g, 2.44 mmol) was stirred at room temperature for 24 h. The mixture was pored into water/brine and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (CH2Cl2/hexanes/EtOAc/MeOH 5/3.5/1/0.05) gave an off-white solid (0.19 g, 42% yield, m.p. 192-194° C.); MS m/e 226 (M−H)+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography (CH2Cl2/hexanes/EtOAc/MeOH 5/3.5/1/0.05)

Quellen und Nachweise

ORD-Eintrag
ord-0012fe911cf944efb5f5fd1d1c66166c
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884814B2

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