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

HRID 30977노트

반응식

HRID 30977 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-87f0c78e6581409aafe2d4313913c391
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425552B2

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