Water → Ethyl 2-(2,3-Difluoro-5-iodobenzoyl)-3-ethoxy-2-propenoate

HRID 1168516

反応式

HRID 1168516 の反応式
O.[F:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([I:10])=[CH:5][C:4]=1[C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:19]([O:21][CH:22](OCC)OCC)[CH3:20].C(OC(=O)C)(=O)C>C(O)C.C(OCC)(=O)C>[F:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([I:10])=[CH:5][C:4]=1[C:11]([C:12](=[CH:22][O:21][CH2:19][CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:18]

参加物

7

反応物 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 12083041Ethyl 3-(2,3-difluoro-5-iodophenyl)-3-oxopropanoate

生成物 1

HCID 69879816Ethyl 2-(2,3-Difluoro-5-iodobenzoyl)-3-ethoxy-2-propenoate収率 98.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

A flask equipped with a Dean-Stark trap and cold water condenser, is charged with ethyl 3-(2,3-difluoro-5-iodophenyl)-3-oxopropanoate (Preparation 20, 14.8 g), triethylorthoformate (12.4 g), and acetic anhydride (14.92 g). The contents are placed in an oil bath initially at 115° C. and the temperature quickly raised to 150° C. where it is maintained until the volume of ethyl acetate and ethanol distillate collected remained constant (ca. 1.25 h). The reaction mixture is cooled and concentrated at reduced pressure to obtain 16.86 g (98.5%) of the title compound as a dark golden oil. Physical characteristics: 1H NMR (CDCl3) δ8.98, 7.87-7.75, 7.71, 7.69-7.51, 4.36, 4.29-4.08, 3.75, 1.48, 1.35, 1.26, 1.21-1.02; MS (ESI+) m/z 411 (M+H)+.

後処理

  1. customThe contents are placed in an oil bath initially at 115° C.
  2. customcollected
  3. custom(ca. 1.25 h)
  4. temperatureThe reaction mixture is cooled
  5. concentrationconcentrated at reduced pressure

出典と根拠

ORDレコード
ord-fe06ed0facec4eed93cda41113b0413c
出典データセット
uspto-grants-2003_09
特許番号
US06624159B2

関連ノート

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