Dicyclohexylcarbodiimide → 1-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-(z-octadeca-9-enoyloxy)propane

HRID 2116415Notes

Reaction equation

HRID 2116415 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:35][CH2:36][CH2:37][CH2:38][OH:39])(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[C:40](O)(=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]/[CH:48]=[CH:49]\[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCCCCC>[C:16]([O:35][CH2:36][CH2:37][CH2:38][O:39][C:40](=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]/[CH:48]=[CH:49]\[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 445639Oleic AcidHCID 103371121-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

Product 1

HCID 867589491-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-(z-octadeca-9-enoyloxy)propane

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 1,3-dicyclohexylcarbodiimide (23.7 g) and 4-(N,N-dimethylamino)pyridine (15.9 g) in methylene chloride (200 ml) was added to a solution of 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane (33.6 g) and z-octadeca-9-enoic acid (30 g) in methylene chloride (400 ml) under nitrogen at room temperature. On completion of reaction as evidenced by tic analysis the solution was diluted with hexane, filtered, concentrated and purified by dry column chromatography to yield 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-(z-octadeca-9-enoyloxy)propane as a free flowing pale yellow oil.

Workup

  1. customOn completion of reaction
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified
  5. customby dry column chromatography

Sources & evidence

ORD record
ord-3d5dbabf7ae04d278f574405b790f6bf
Source dataset
uspto-grants-2008_10
Patent number
USRE040546E1

Reaction notes

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