Acetyl chloride → 2-Methyl-benzooxazole-4-carboxylic acid ethyl ester

HRID 882790

Reaktionsgleichung

Reaktionsgleichung von HRID 882790
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=1[NH2:12])[CH3:2].[C:14](Cl)(=O)[CH3:15].CCN(CC)CC.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]2[O:11][C:14]([CH3:15])=[N:12][C:6]=12)=[O:13])[CH3:2]

Komponenten

7

Edukt 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 14167647Ethyl 2-amino-3-hydroxybenzoate

Produkt 1

HCID 593168402-Methyl-benzooxazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7237O-XyleneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-3-hydroxy-benzoic acid ethyl ester (5.52 mmol; J. Reisch, G. M. K. B. Gunaherath Monatshefte für Chemie, 1988, 119, 1169-1178), acetyl chloride (6.07 mmol), NEt3 (6.07 mmo) and pyridinium p-toluenesulfonate (1.47 mmol) in xylene (60 mL) is heated at reflux for 16 h, cooled to rt, diluted with EtOAc and washed with water. The organic layer is dried over MgSO4 and concentrated in vacuo to give a crude product which is purified by flash chromatography (gradient: heptane to heptane/EtOAc 6/4). LC-MS: tR=0.81 min; [M+H]+=206.0.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 16 h
  3. washwashed with water
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9c140c3a7bd94a99b0ac4d9bdce1a0ac
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236801B2

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