Toluene → Ethyl beta-(2-methylpyridin-3-yl)acrylate

HRID 963320Notes

Reaction equation

HRID 963320 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][N:3]=1.C(OP([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(OCC)=O)C.[H-].[Na+].[C:26]1(C)C=CC=CC=1>>[CH3:26][C:4]1[C:5]([CH:8]=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][CH:7]=[CH:2][N:3]=1

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 101925666-Methyl-3-pyridinecarboxaldehyde

Product 1

HCID 54522417Ethyl beta-(2-methylpyridin-3-yl)acrylate

Procedure

A solution of 0.55 g (4.54 mmol) of 2-methylpyridin-5-carboxaldehyde in toluene was added dropwise into a cool suspension of 1.12 g (5 mmol) of ethyl diethylphosphonoacetate and 0.12 g (5 mmol) of NaH in toluene and the resulting solution was allowed to react at 65° C. for 30 min. After cooling, the mixture was filtered through SUPERCEL™ (wash SUPERCEL™ with ether) and concentrated in vacuo to yield 0.71 g (87.6%c) of ethyl β-(2-methylpyridin-3-yl)acrylate (cis/trans mixture), which was further purified through a silica plug (hexane/ethyl acetate, 1:1).

Workup

  1. customto react at 65° C. for 30 min
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through SUPERCEL™ (wash SUPERCEL™ with ether)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2dc01e6f17014aa18fbe30546cb5eba5
Source dataset
uspto-grants-1998_06
Patent number
US05763461

Reaction notes

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