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

HRID 560309노트

반응식

HRID 560309 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 7237O-Xylene용매HCID 8857Ethyl Acetate용매

실험 절차

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 mmol) 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 FC (gradient: heptane to heptane/EtOAc 6/4). LC-MS: tR=0.81 min; [M+H]+=206.0.

후처리

  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

출처 및 근거

ORD 기록
ord-cbc19d47ea45452a908bf20c817ba802
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063099B2

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