Reaktion #2467920

ord-f53d919e2e6047bf8a7481d8565fcec9

Reaktionsgleichung

CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)Cl
z,z,z-octadeca-6,9,12-trienoyl chloride
Cc1ncc(CO)c(CO)c1O.Cl
pyridoxine hydrochloride
CCN(CC)CC
triethylamine
CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)OCc1cnc(C)c(O)c1COC(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC
2-methyl-3-hydroxy-4,5-di(z,z,z-octadeca-6,9,12-trienoyloxy)methyl pyridine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstige(4 h)
  2. 2
    Einengenwas concentrated
  3. 3
    Sonstigepurified by flash chromatography (ethyl acetate/hexane)

Vorschrift

A solution of z,z,z-octadeca-6,9,12-trienoyl chloride (650 mg, 2.2 mmol) in methylene chloride (10 ml) was added slowly dropwise to a mixture of pyridoxine hydrochloride (206 mg, 1 mmol), triethylamine (0.7 ml, 5 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 tic, (4 h) the mixture was concentrated and purified by flash chromatography (ethyl acetate/hexane), yielding 2-methyl-3-hydroxy-4,5-di(z,z,z-octadeca-6,9,12-trienoyloxy)methyl pyridine as a colourless oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE043632E1uspto-grants-2012_09