反应 #56587

ord-fef7741e30834de381e17cd8e64dcbf6

反应方程式

CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)Cl
z,z,z-octadeca-6,9,12-trienoyl chloride
Cc1ncc(CO)c(C=O)c1O.Cl
pyridoxal hydrochloride
CCN(CC)CC
triethylamine
CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)OCc1cnc(C)c(O)c1C=O
2-methyl-3-hydroxy-4-formyl-5-(z,z,z-octadeca-6,9,12-trienoyloxy)methyl pyridine

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    浓缩the mixture was concentrated
  2. 2
    其他purified by flash chromatography (ethyl acetate/hexane)

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: USRE040480E1uspto-grants-2008_09