Lithium iodide → HCID 86733777, compound

HRID 1282836Notes

Reaction equation

HRID 1282836 reaction equation
[I-].[Li+].[CH3:3][C:4]([CH3:27])([CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:5]([O:7]C)=[O:6]>N1C(C)=CC(C)=CC=1C>[CH3:3][C:4]([CH3:27])([CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 66321Lithium iodide2×HCID 86733778HCID 86733778, compound

Product 1

HCID 86733777HCID 86733777, compound

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent2×

Procedure

The instant compounds having the 5, 8, 11 and 14 double bonds are prepared preferably by alkylating the appropriate alkyl ester of arachidonic acid with an alkyl iodide in the presence of a base, such as a secondary amine, and n-alkyl lithium, i.e. n-butyl lithium. Typically, ethyl arachidonate is added to n-isopropylcyclohexylamine containing n-butyl lithium at a low temperature, e.g. -78°C., and then methyl iodide is added to yield ethyl 2-methylarachidonate. That same procedure then is repeated with ethyl 2-methylarachidonate in place of ethyl arachidonate to yield ethyl 2,2-dimethylarachidonate. The ester moiety can be cleaved with lithium iodide in an aromatic amine, e.g. collidine, to yield the corresponding acid. For example, methyl 2,2-dimethylarachidonate, when treated with lithium iodide in collidine, affords 2,2-dimethyl arachidonic acid.

Workup

  1. customto yield the corresponding acid

Sources & evidence

ORD record
ord-e1bbba5732b340da94134acc1eb21189
Source dataset
uspto-grants-1976_08
Patent number
US03972907

Reaction notes

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