反応 #2467915

ord-cba0619bc7ab4e268f471b6b7eaf376c

反応方程式

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

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    ろ過The reaction was filtered
  2. 2
    濃縮concentrated
  3. 3
    その他purified by flash chromatography (ethyl acetate/hexane)

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: USRE043632E1uspto-grants-2012_09