Dabco → HCID 11716214, 화합물

HRID 1983584노트

반응식

HRID 1983584 반응식
[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]

참가 물질

5

반응물 3

HCID 9237DabcoHCID 103713-PyridinecarboxaldehydeHCID 2934614-Chlorophenyl acrylate

생성물 1

HCID 11716214HCID 11716214, 화합물수율 18%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4d3c7e8fe3934b86938f164ec8048609
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07541472B2

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