Реакция #2467915

ord-cba0619bc7ab4e268f471b6b7eaf376c

Уравнение реакции

CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoic acid
OCCCO
1,3-propane diol
C(=NC1CCCCC1)=NC1CCCCC1
1,3-dicyclohexylcarbodiimide
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)OCCCO
1-(z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoyloxy)-3-hydroxypropane

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ФильтрацияThe reaction was filtered
  2. 2
    Концентрированиеconcentrated
  3. 3
    Другоеpurified by flash chromatography (ethyl acetate/hexane)

Методика

A solution of z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoic acid (6.4 g, 19.5 mmol) in methylene chloride (225 ml) was added dropwise to a solution of 1,3-propane diol (7.5 g, 99 mmol), 1,3-dicyclohexylcarbodiimide (4.65 g, 20 mmol) and 4-(N,N-dimethylamino)pyridine (2.1 g, 17 mmol) in methylene chloride (225 ml) at −10° C. The reaction mixture was stirred overnight, warming up to room temperature. The reaction was filtered, concentrated and purified by flash chromatography (ethyl acetate/hexane) to yield 1-(z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoyloxy)-3-hydroxypropane as a pale yellow oil.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: USRE043632E1uspto-grants-2012_09