Pyridine → HCID 68008707, compound

HRID 1259012Notes

Reaction equation

HRID 1259012 reaction equation
[CH2:1]([C:18]([OH:56])([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]/[CH:46]=[CH:47]\[CH2:48]/[CH:49]=[CH:50]\[CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH:19]([OH:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].N1C=CC=CC=1.[O:63]=[C:64](Cl)OC(Cl)(Cl)Cl>CCOCC>[CH2:1]([C:18]1([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]/[CH:46]=[CH:47]\[CH2:48]/[CH:49]=[CH:50]\[CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[O:37][C:64](=[O:63])[O:56]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10426DiphosgeneHCID 86667535HCID 86667535, compound

Product 1

HCID 68008707HCID 68008707, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (6Z,9Z,28Z,31Z)-19-((8Z,11Z)-heptadeca-8,11-dienyl)heptatriaconta-6,9,28,31-tetraene-18,19-diol (540 mg, 0.67 mmol) in anhydrous ether (5 mL) was added pyridine (81 μL, 1.0 mmol). To this solution was added diphosgene (132 μL, 1.1 mmol) slowly over 5 minutes. The solution was stirred for 2 hours at room temperature then concentrated in vacuo to dryness and purified by column chromatography on silica gel 60 (eluted with 5% ether in hexanes) to afford 4,5-di((8Z,11Z)-heptadeca-8,11-dienyl)-4-((9Z,12Z)-octadeca-9,12-dienyl)-1,3-dioxolan-2-one as a colorless oil (310 mg, 57%).

Workup

  1. concentrationthen concentrated in vacuo to dryness
  2. custompurified by column chromatography on silica gel 60 (eluted with 5% ether in hexanes)

Sources & evidence

ORD record
ord-e4472d8926ce4cd59bd92cfc7a785da2
Source dataset
uspto-grants-2013_06
Patent number
US08466122B2

Reaction notes

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