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DBU → HCID 17952717,化合物

HRID 1394635
笔记
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反应方程式

HRID 1394635 反应方程式
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[C:2]1[CH:8]=O.COP([CH:16]([NH:20]C(=O)C)[C:17](=[O:19])[CH3:18])(=O)OC.C1CCN2C(=NCCC2)CC1>ClCCl>[S:1]1[C:2]2=[CH:8][N:20]=[C:16]([C:17](=[O:19])[CH3:18])[CH:6]=[C:3]2[CH:4]=[CH:5]1
参与物实验过程后处理来源与证据反应笔记

参与物

5

反应物 3

HCID 81184DBUHCID 573752噻吩-2,3-二甲醛HCID 10900225HCID 10900225,化合物

产物 1

HCID 17952717HCID 17952717,化合物收率 43%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

A solution of 2,3-thiophenedicarboxaldehyde (600 mg, 4.28 mmol) in dichloromethane (50 ml) was cooled to 0° C. under an atmosphere of nitrogen. (1-Acetylamino-2-oxo-propyl)-phosphonic acid dimethyl ester (1.05 g, 4.70 mmol) was added [literature procedure: Kitamura, et al. Tet. Lett., 36(32), 1995, pp. 5769-5772], followed by DBU (0.471 ml, 4.70 mmol), and the mixture allowed to warm to ambient temperature overnight, then concentrated in vacuo, and the residue was then purified by flash chromatography (0-50% ethyl acetate in hexanes) to provide 1-thieno[2,3-c]pyridin-5-yl-ethanone as a white solid (326 mg, 43%). 1HNMR (250 MHz, CDCl3): δ 9.20 (s, 1H), 8.50 (d, 1H, J=1.02), 7.80 (d, 1H, J=5.36), 7.51 (d, 1H, J=5.36), 2.81 (s, 3H).

后处理

  1. concentrationconcentrated in vacuo
  2. customthe residue was then purified by flash chromatography (0-50% ethyl acetate in hexanes)

来源与证据

ORD记录
ord-ecfad03223024fe8b8e611a8e1550ebe
来源数据集
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
专利号
US07348359B2

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记