Methyl iodide → HCID 86733776, compound

HRID 1282837Notes

Reaction equation

HRID 1282837 reaction equation
[CH3:1]CCCCC.C([Li])CCC.[C:12]([O:33][CH2:34][CH3:35])(=[O:32])[CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].CI>O1CCCC1>[CH3:1][CH:13]([CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:12]([O:33][CH2:34][CH3:35])=[O:32]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5367369Ethyl arachidonateHCID 178418244HCID 178418244, compound

Product 1

HCID 86733776HCID 86733776, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.7 g. of n-isopropylcyclohexylamine in 15 ml. of tetrahydrofuran, at -78°, is added 5.5 ml. of a 2.4 N n-butyl lithium n-hexane solution. Then 3 g. of ethyl arachidonate in 150 ml. of tetrahydrofuran is added dropwise, over a 2-hour period, at -78°. Then 1.5 ml. of methyl iodide is added and the mixture is allowed to warm to room temperature. The solution is concentrated by evaporating tetrahydrofuran, then extracted with ether to yield ethyl 2-methylarachidonate.

Workup

  1. concentrationThe solution is concentrated
  2. customby evaporating tetrahydrofuran
  3. extractionextracted with ether

Sources & evidence

ORD record
ord-c8b4fd74ce794077b094c1624a1e0747
Source dataset
uspto-grants-1976_08
Patent number
US03972907

Reaction notes

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