Toluene → HCID 87310612, compound

HRID 508659Notes

Reaction equation

HRID 508659 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5](C=O)=[CH:4][N:3]=1.[C:11]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:13][CH2:14][CH3:15])=[O:12].[C:36]1(C)C=CC=CC=1>>[Cl:8][C:7]1[CH:6]=[CH:5][C:4](/[CH:36]=[CH:16]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:3][C:2]=1[Cl:1]

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 115356545,6-Dichloropyridine-3-carbaldehyde

Product 1

HCID 87310612HCID 87310612, compoundYield 16%

Procedure

A solution of crude 2,3-dichloro-5-formylpyridine and (carbethoxymethylene)triphenylphosphorane (2.14 g, 5.83 mmol) in toluene (12 mL) was heated at reflux overnight and then cooled to room temperature. After solvent removal at reduced pressure, the residue was chromatographed (9% to 10% EtOAc/hexane) to give 323 mg (16% from 5,6-dichloro-3-pyridinemethanol) of ethyl(E)-3-(5,6-dichloro-2-pyridinyl)-2-propenoate as a white solid, mp 102-103° C. IR 2914, 1702, 1428, 1193 cm−1; 1H NMR (CDCl3) δ 1.37 (t, J=7.2 Hz, 3H, OCH2CH3), 4.31 (q, J=7.2 Hz, 2H, OCH2CH3), 6.53 (d, J=16.2 Hz, 1H, CH═CHCO), 7.62 (d, J=16.2 Hz, 1H, CH═CHCO), 7.94 (d, J=1.8 Hz, 1H, 4-ArH), 8.44 ppm (d, J=1.8 Hz, 1H, 2-ArH). HRMS calcd C10H9Cl2NO2 [M+H]+ 246.0083. found 246.0086.

Workup

  1. temperatureat reflux overnight
  2. customAfter solvent removal at reduced pressure
  3. customthe residue was chromatographed (9% to 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-2ddb76cd3a2042c4824fca0fc1ce7907
Source dataset
uspto-grants-2015_08
Patent number
US09096544B2

Reaction notes

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