2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal → (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-ol

HRID 1259007Notes

Reaction equation

HRID 1259007 reaction equation
[CH2:1]([O:19][CH:20]([CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:21]=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C(OCC)C>[CH2:25]([O:24][CH2:23][CH:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:21]([OH:22])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

3

Reactant 1

HCID 866675312,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal

Product 1

HCID 86667532(12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-olYield 41.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal (1.5 g, 2.62 mmol) in anhydrous diethyl ether (10 mL) was added LinMgBr Grignard (2.56 mL, 5.23 mmol). Upon completion, the solution was quenched with 5% HCl (50 mL) and washed with diethyl ether (3×50 mL). The combined ethyl ether extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (eluted with a gradient of 100% hexanes to 2% ethyl acetate in hexanes) to afford (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-ol as a colorless oil (460 mg, 21%).

Workup

  1. customUpon completion, the solution was quenched with 5% HCl (50 mL)
  2. washwashed with diethyl ether (3×50 mL)
  3. dry with materialThe combined ethyl ether extracts were dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to dryness
  6. customThe residue was purified by column chromatography on silica gel 60 (
  7. washeluted with a gradient of 100% hexanes to 2% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e86d404cd86c4373b20a43cd74db9be4
Source dataset
uspto-grants-2013_06
Patent number
US08466122B2

Reaction notes

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