Tetramethylammonium hydroxide → HCID 86740085, compound

HRID 462393Notes

Reaction equation

HRID 462393 reaction equation
[C:1]([OH:22])(=[O:21])[CH2:2][CH2:3][CH:4]=[C:5]=[CH:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[OH-].[CH3:24][N+](C)(C)C>CO>[C:1]([O:22][CH3:24])(=[O:21])[CH2:2][CH2:3][CH:4]=[C:5]=[CH:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 60966Tetramethylammonium hydroxideHCID 13470484HCID 13470484, compound

Product 1

HCID 86740085HCID 86740085, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 300 mg of 4,5,8Z-eicosatrienoic acid was treated with 0.52 ml of a 20% solution of tetramethylammonium hydroxide in methanol. After stirring for 5 minutes at room temperature the methanol was evaporated under reduced pressure at 30 C. and 5 ml of dimethyl formamide was then added. The resulting suspension was stirred and treated with 0.25 g of methyl iodide. After 30 minutes at room temperature the reaction mixture was diluted with 30 ml of water and extracted with 100 ml of ether. The ethereal solution was washed with water and brine and then dried over sodium sulfate. Evaporation of the ether gave methyl 4,5,8Z-eicosatrienoate.

Workup

  1. customwas evaporated under reduced pressure at 30 C
  2. additionand 5 ml of dimethyl formamide was then added
  3. additiontreated with 0.25 g of methyl iodide
  4. additionAfter 30 minutes at room temperature the reaction mixture was diluted with 30 ml of water
  5. extractionextracted with 100 ml of ether
  6. washThe ethereal solution was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the ether

Sources & evidence

ORD record
ord-ce0cbfab5a44411088fd78ed3f8ea65f
Source dataset
uspto-grants-1985_05
Patent number
US04515727

Reaction notes

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