Benzyl Chloride → 6-Benzyloxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester

HRID 556342

Reaktionsgleichung

Reaktionsgleichung von HRID 556342
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O.CCOC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2]

Komponenten

7

Edukt 3

HCID 7503Benzyl ChlorideHCID 10796Cesium carbonateHCID 136216618Ethyl 6-hydroxybenzo[d]isoxazole-3-carboxylate

Produkt 1

HCID 669926006-Benzyloxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
56 °C

Versuchsvorschrift

To a solution of 0.98 g (4.73 mMol) 6-hydroxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester [preparation see: J. Am. Chem. Soc. 97 (1974), 7305] in 100 ml acetone, 545 μl (4.73 mMol) benzylchloride, 3.08 g (9.46 mMol) Cs2CO3 und 10 mg NaI are added. Then the mixture is stirred for 2 h at rt and 5 h at 56° C. The reaction mixture is diluted with EtOAc and water, the aq. phase separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated after addition of 10 g SiO2. The resulting powder is put on top of a chromatography column (SiO2) and the title compound eluated with hexan/EtOAc 9:1→8:2→7:3: MS: [M+1]+=298; TLC(hexane/EtOAc 3:1): Rf=0.54.

Aufarbeitung

  1. customthe aq. phase separated off
  2. extractionextracted with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. additionafter addition of 10 g SiO2

Quellen und Nachweise

ORD-Eintrag
ord-d50dad6058f1460a8e5533089bfa5bdd
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058276B2

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