Dabco → HCID 11716214、化合物

HRID 1983584ノート

反応式

HRID 1983584 の反応式
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)(=[O:4])[CH:2]=[CH2:3].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[O:20])[CH:14]=1.C1N2CCN(CC2)C1>ClCCl>[OH:20][CH:19]([C:15]1[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=1)[C:2](=[CH2:3])[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:4]

参加物

5

反応物 3

HCID 9237DabcoHCID 103713-PyridinecarboxaldehydeHCID 2934614-Chlorophenyl acrylate

生成物 1

HCID 11716214HCID 11716214、化合物収率 18%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 37 mg (0.20 mmol) of 4-chlorophenyl acrylate, 22 mg (0.22 mmol) of pyridine-3-carboxaldehyde, and 22 mg (0.20 mmol) of DABCO was thoroughly shaken on a Vortex mixer. After 1 hr at room temperature, the mixture was diluted with dichloromethane. The DCM solution was washed with dilute aqueous acetic acid, and the DCM removed by rotoevaporation. The residue was purified by preparative HPLC to give 10 mg (0.035 mmol, 18% yield) of the desired Baylis-Hillman adduct, 4-chlorophenyl β-hydroxy-α-methylene-3-pyridinepropanoate. 1H NMR (CDCl3): δ 5.70 (1H), 6.14 (1H), 6.64 (1H), 7.76 (d of t, 1H), 8.55 (d of d, 1H), and 8.64 ppm (d, 1H). MS m/z: 290.0 (M+H).

後処理

  1. washThe DCM solution was washed with dilute aqueous acetic acid
  2. customthe DCM removed by rotoevaporation
  3. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-4d3c7e8fe3934b86938f164ec8048609
出典データセット
uspto-grants-2009_06
特許番号
US07541472B2

反応ノート

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