Ethyl 2-thiopheneglyoxylate → [(3-Methyl-butyl)-hydrazono]-thiophen-2-yl-acetic acid ethyl ester

HRID 30977

反応式

HRID 30977 の反応式
[CH2:1]([O:3][C:4](=[O:12])[C:5](=O)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[CH3:2].[CH3:13][CH:14]([CH3:19])[CH2:15][CH2:16][NH:17][NH2:18]>C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5](=[N:18][NH:17][CH2:16][CH2:15][CH:14]([CH3:19])[CH3:13])[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[CH3:2]

参加物

4

反応物 2

HCID 77693Ethyl 2-thiopheneglyoxylateHCID 18696583(3-Methylbutyl)hydrazine

生成物 1

HCID 72562995[(3-Methyl-butyl)-hydrazono]-thiophen-2-yl-acetic acid ethyl ester収率 47.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To a solution of oxo-thiophen-2-yl-acetic acid ethyl ester (1d) (3.97 g, 21.6 mmol) in absolute ethanol (100 mL), (3-Methyl-butyl)-hydrazine (2b) (2.0 g, 19.6 mmol) was added. The mixture was stirred at 80° C. under N2 atmosphere for 2-25 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel to give the desired product (3d) (2.48 g) that was directly used in the next step. LC-MS (ESI+): m/e 269.2 [M+1]+, 537.4 [2M+1]+, 559.0 [2M+Na]+ (exact ms: 268.12).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-87f0c78e6581409aafe2d4313913c391
出典データセット
uspto-grants-2008_09
特許番号
US07425552B2

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