Dimethylformamide → HCID 54049871, compound

HRID 2164182Notes

Reaction equation

HRID 2164182 reaction equation
[C:1]([CH2:5]P(=O)(OCC)OCC)([O:3][CH3:4])=[O:2].CN(C)C=O.[H-].[Na+].[CH3:21][C:22]([CH2:30][CH3:31])=[CH:23][CH2:24][CH2:25][CH2:26][C:27](=O)[CH3:28]>O>[CH3:28][C:27]([CH2:26][CH2:25][CH2:24][CH:23]=[C:22]([CH3:21])[CH2:30][CH3:31])=[CH:5][C:1]([O:3][CH3:4])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 54017105HCID 54017105, compound

Product 1

HCID 54049871HCID 54049871, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 11.2 g. of diethyl carbomethoxymethylphosphonate in 100 ml. of dimethylformamide is treated with 2.4 g. of sodium hydride. The mixture is stirred until the evolution of gas ceases and then 10 g. of 7-methyl-6-nonen-2-one is added slowly with stirring, maintaining temperature below 30°. The mixture is stirred for about one hour, then diluted with water and then extracted with ether. The ethereal phase is washed with water, dried over sodium sulfate and evaporated under reduced pressure to yield methyl 3,8-dimethyldeca-2,7-dienoate as a mixture of isomers (trans,cis; trans,trans; cis,cis and cis,trans) which are separated by chromatography.

Workup

  1. additionA mixture of 11.2 g
  2. stirringwith stirring
  3. temperaturemaintaining temperature below 30°
  4. stirringThe mixture is stirred for about one hour
  5. extractionextracted with ether
  6. washThe ethereal phase is washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6a874b5230b94ef291be9b77086adcb3
Source dataset
uspto-grants-1979_01
Patent number
US04137273

Reaction notes

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