Pyridoxal hydrochloride → Ethyl 3-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridyl)acrylate hydrochloride

HRID 868357Notes

Reaction equation

HRID 868357 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH:9]=O)[C:5]([CH2:11][OH:12])=[CH:4][N:3]=1.[ClH:13].[C:14]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[ClH:13].[OH:8][C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[C:5]([CH2:11][OH:12])[C:6]=1[CH:9]=[CH:19][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 6171Pyridoxal hydrochlorideHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 67938271Ethyl 3-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridyl)acrylate hydrochlorideYield 23.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 10.0 g of pyridoxal hydrochloride in 400 ml of ethanol, 17.2 g of (carbethoxymethylene)triphenylphosphorane is added under cooling in an ice-water bath, and the mixture is stirred at room temperature for 17 hours. The reaction mixture is concentrated to half in volume and cooled in an ice-water bath. The precipitate is collected and washed with a small amount of cold ethanol to give 3.2 g of ethyl 3-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridyl)acrylate hydrochloride.

Workup

  1. additionis added
  2. temperatureunder cooling in an ice-water bath
  3. concentrationThe reaction mixture is concentrated to half in volume
  4. temperaturecooled in an ice-water bath
  5. customThe precipitate is collected
  6. washwashed with a small amount of cold ethanol

Sources & evidence

ORD record
ord-e6095107ac334040a1b1ae70097ba0d8
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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