Dabco → HCID 11716214, compound

HRID 1983584Notes

Reaction equation

HRID 1983584 reaction equation
[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]

Participants

5

Reactant 3

HCID 9237DabcoHCID 103713-PyridinecarboxaldehydeHCID 2934614-CHLOROPHENYL ACRYLATE

Product 1

HCID 11716214HCID 11716214, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4d3c7e8fe3934b86938f164ec8048609
Source dataset
uspto-grants-2009_06
Patent number
US07541472B2

Reaction notes

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