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

HRID 2116417Notes

Reaction equation

HRID 2116417 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-123d629738eb470b94aa5d1dc83a266f
Source dataset
uspto-grants-2008_10
Patent number
USRE040546E1

Reaction notes

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