Reaction #56587

Reaction equation

z,z,z-octadeca-6,9,12-trienoyl chloride

pyridoxal hydrochloride

triethylamine

→

2-methyl-3-hydroxy-4-formyl-5-(z,z,z-octadeca-6,9,12-trienoyloxy)methyl pyridine

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Concentrationthe mixture was concentrated
2. 2
   Otherpurified by flash chromatography (ethyl acetate/hexane)

Procedure

A solution of z,z,z-octadeca-6,9,12-trienoyl chloride (800 mg, 2.7 mmol) in methylene chloride (10 ml) was added slowly dropwise to a mixture of pyridoxal hydrochloride (500 mg, 2.45 mmol), triethylamine (1 ml, 7.2 mmol) and 4-(N,N-dimethylamino)pyridine (few mg, catalytic amount) in methylene chloride (20 ml) at 0° C. under nitrogen. On completion, as indicated by tlc, the mixture was concentrated and purified by flash chromatography (ethyl acetate/hexane), yielding 2-methyl-3-hydroxy-4-formyl-5-(z,z,z-octadeca-6,9,12-trienoyloxy)methyl pyridine as a colourless oil which subsequently solidified.

Source