Diethyl Ether → HCID 86667528, compound

HRID 1259000Notes

Reaction equation

HRID 1259000 reaction equation
[Mg].[CH2:2](Br)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH2:21]([O:39][CH:40]1[CH2:44][CH2:43][O:42][C:41]1=[O:45])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].C(O[CH2:49][CH3:50])C>>[CH2:2]([C:41]([OH:45])([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]/[CH:9]=[CH:8]\[CH2:7]/[CH:6]=[CH:5]\[CH2:4][CH2:3][CH2:2][CH2:49][CH3:50])[CH:40]([O:39][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:44][CH2:43][OH:42])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 5462224MagnesiumHCID 10065142(6Z,9Z)-18-bromooctadeca-6,9-dieneHCID 680092053-((9Z,12Z)-octadeca-9,12-dienyloxy)dihydrofuran-2(3H)-one

Product 1

HCID 86667528HCID 86667528, compoundYield 56%

Procedure

A 100 mL round bottom flask charged with magnesium turnings (250 mg) and a stir bar was dried with a heat gun for 5 minutes then cooled under nitrogen. The flask was charged with dry THF (10 mL) and a small grain of iodine. A solution of linoleyl bromide (3 g, 9.1 mmol) in diethyl ether was added slowly and the mixture was stirred at room temperature. The Grignard did not initiate so the solution was concentrated to ˜5 mL then stirred for 2 minutes until the solution turned opaque and the iodine color disappeared. After 20 minutes, a colorless solid precipitated so the reaction was diluted with THF (15 mL) and stirred overnight. The next day 3-((9Z,12Z)-octadeca-9,12-dienyloxy)dihydrofuran-2(3H)-one (1.3 g, 3.6 mmol) was added and the solution was stirred for 3 hours. The reaction was diluted with ether (100 mL) and washed with 5% HCl (50 mL). The ether layer was dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (eluted with 10% ether in hexanes) to afford (14Z,17Z)-4-((9Z,12Z)-octadeca-9,12-dienyl)-3-((9Z,12Z)-octadeca-9,12-dienyloxy)tricosa-14,17-diene-1,4-diol as a colorless oil (1.75 g, 56%).

Workup

  1. customwas dried with a heat gun for 5 minutes
  2. temperaturethen cooled under nitrogen
  3. additionThe flask was charged with dry THF (10 mL)
  4. concentrationwas concentrated to ˜5 mL
  5. stirringthen stirred for 2 minutes until the solution
  6. customa colorless solid precipitated so the reaction
  7. additionwas diluted with THF (15 mL)
  8. stirringstirred overnight
  9. stirringthe solution was stirred for 3 hours
  10. washwashed with 5% HCl (50 mL)
  11. dry with materialThe ether layer was dried on magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo to dryness
  14. customThe residue was purified by column chromatography on silica gel 60 (eluted with 10% ether in hexanes)

Sources & evidence

ORD record
ord-8f31361b97a84846942eea42cf1c803a
Source dataset
uspto-grants-2013_06
Patent number
US08466122B2

Reaction notes

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