Pyridoxal → 3-(3-Hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-acrylic acid ethyl ester

HRID 1158943Notes

Reaction equation

HRID 1158943 reaction equation
[C:1]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[CH3:26][C:27]1[N:32]=[CH:31][C:30]([CH2:33][OH:34])=[C:29]([CH:35]=O)[C:28]=1[OH:37].C(N(CC)CC)C>C1COCC1>[CH2:4]([O:3][C:1](=[O:2])[CH:6]=[CH:35][C:29]1[C:30]([CH2:33][OH:34])=[CH:31][N:32]=[C:27]([CH3:26])[C:28]=1[OH:37])[CH3:5]

Participants

5

Reactant 3

HCID 1050PyridoxalHCID 8471TriethylamineHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 543009153-(3-Hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-acrylic acid ethyl esterYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A clear solution of (carbethoxymethylene)triphenylphosphorane (22.3 g, 64.02 mmol) in THF was added to pyridoxal (13.01 g, 64.0 mmol) in THF at room temperature. The mixture was stirred for one hour, then triethylamine (10 mL) was added and the mixture was stirred until the solution turned to a yellow suspension. The solvent was evaporated, and the crude product purified by column chromatography on silica gel using a mixture of dichloromethane:methyl alcohol (20:1) as eluant to give 3-(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-acrylic acid ethyl ester (34) (15.2 g, quantitative yield) as a yellow solid.

Workup

  1. stirringthe mixture was stirred until the solution
  2. customThe solvent was evaporated
  3. customthe crude product purified by column chromatography on silica gel using
  4. additiona mixture of dichloromethane:methyl alcohol (20:1) as eluant

Sources & evidence

ORD record
ord-719fb5e549854a3ca4920cc770418dab
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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