Methyl arachidonate → Arachidonyl alcohol

HRID 733481Notes

Reaction equation

HRID 733481 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CCOCC>[CH2:9]([OH:8])[CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 6421258Methyl arachidonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10891603Arachidonyl alcoholYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a magnetically stirred solution of 0.5 ml (0.5 mmol) of LiAlH4 in Et2O, 100 mg (0.314 mmol) of arachidonic acid methyl ester in 2 mL of Et2O was added dropwise at 0° C. The reaction mixture was stirred for 1 h and then quenched by addition of 1 mL of EtOAC. 2 mL of saturated NH4Cl solution was added and the organic layer was separated, dried with MgSO4, filtered and evaporated. Chromatography on silica gel (eluents: CH2Cl2/petroleum ether up to 70% CH2Cl2), evaporation, followed by Millipore filtration of a CH2Cl2 solution of the product gave 99.3 mg (0.292 mmol, 93% yield) of arachidonyl alcohol as a colorless oil: TLC (CHCl3) Rf 0.28; 1H NMR (200 MHz, CDCl3) δ 5.37 (m, 8 H ), 3.61 (t, 2 H, J=6 Hz), 2.79 (m, 6H), 2.08 (m, 4 H), 1.66-1.17 (m, 8 H), 0.92 (t, 3 H, J=7 Hz).

Workup

  1. customquenched by addition of 1 mL of EtOAC
  2. addition2 mL of saturated NH4Cl solution was added
  3. customthe organic layer was separated
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customChromatography on silica gel (eluents: CH2Cl2/petroleum ether up to 70% CH2Cl2), evaporation
  8. filtrationfollowed by Millipore filtration of a CH2Cl2 solution of the product

Sources & evidence

ORD record
ord-e9d33d028df34320b2b08ba7f7ce8958
Source dataset
uspto-grants-2009_09
Patent number
US07589220B2

Reaction notes

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