Triethylamine → 1-(2,3,5-Triiodobenzoyloxy)-3-(z,z,z-octadeca-6,9,12-trienoyloxy)propane

HRID 28303Notes

Reaction equation

HRID 28303 reaction equation
[I:1][C:2]1[C:10]([I:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:13]([O:32][CH2:33][CH2:34][CH2:35][OH:36])(=[O:31])[CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(N(CC)CC)C>C(Cl)Cl>[I:1][C:2]1[C:10]([I:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([O:36][CH2:35][CH2:34][CH2:33][O:32][C:13](=[O:31])[CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27608062,3,5-Triiodobenzoyl chlorideHCID 103371121-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

Product 1

HCID 691998781-(2,3,5-Triiodobenzoyloxy)-3-(z,z,z-octadeca-6,9,12-trienoyloxy)propane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3,5-Triiodobenzoyl chloride (1.54 g, 3.08 mmol) was added to a mixture of 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane (1 g, 2.97 mmol) and triethylamine (1 ml) in methylene chloride (80 ml) and the resulting mixture stirred overnight at room temperature under nitrogen. The mixture was concentrated and purified by flash chromatography (ethyl acetate/hexane) to yield 1-(2,3,5-triiodobenzoyloxy)-3-(z,z,z-octadeca-6,9,12-trienoyloxy)propane.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5d9d2a5debe44cfc868bec591d19c856
Source dataset
uspto-grants-2008_09
Patent number
USRE040480E1

Reaction notes

Loading…