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

HRID 882790

反応式

HRID 882790 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 7237O-Xylene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c140c3a7bd94a99b0ac4d9bdce1a0ac
出典データセット
uspto-grants-2012_08
特許番号
US08236801B2

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