13058-52-1 → HCID 11565215, compound

HRID 537842Notes

Reaction equation

HRID 537842 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7](OC)(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CCOCC>[CH2:7]([OH:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 1174843613058-52-1HCID 21226445Aluminium lithium hydride

Product 1

HCID 11565215HCID 11565215, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium aluminum hydride (1.5 g, 38.7 mmol) in anhydrous ether (50 mL) cooled to 0° C. under nitrogen was slowly added a solution of (9Z,11E)-methyl octadeca-9,11-dienoate (11.6 g, 38.7 mmol) in anhydrous diethyl ether (50 mL+25 mL rinse) via cannula transfer. The solution was stirred for 2 hours at 0° C. then quenched slowly with 1M NaOH (3.5 mL). The solution was dried on magnesium sulfate, filtered and concentrated in vacuo to dryness to afford the product as a colorless oil (9.5 g, 92%).

Workup

  1. customthen quenched slowly with 1M NaOH (3.5 mL)
  2. customThe solution was dried on magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-6bf3acd359944be5a6cb5e06873c4c6d
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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