Methyl pyruvate → HCID 53921162, compound

HRID 1606680Notes

Reaction equation

HRID 1606680 reaction equation
Br[CH2:2][CH2:3][CH:4]=[C:5]([CH3:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Li])CCC.[C:36]([O:41][CH3:42])(=[O:40])[C:37]([CH3:39])=O>CCCCCC.CCOCC.C1C=CC=CC=1>[CH3:39][C:37](=[CH:2][CH2:3][CH:4]=[C:5]([CH3:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:36]([O:41][CH3:42])=[O:40]

Participants

8

Reactant 4

HCID 11748Methyl pyruvateHCID 11776TriphenylphosphineHCID 54246900HCID 54246900, compoundHCID 178418339Butyllithium

Product 1

HCID 53921162HCID 53921162, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5.0 g. of 1-bromo-4-metyl-3-nonene and 6.35 g. of triphenylphosphine in 25 ml. of dry benzene is heated under reflux for 12 hrs., then the mixture is allowed to cool to 25°C. and 50 ml. of dry ether and 11 ml. of 15% n-butyl lithium in hexane are added. The resulting mixture is stirred for 2 hrs. at 25°C., giving a red solution, then 2.5 g. (2.15 ml.) of methyl pyruvate in 10 ml. of ether is added and the mixture is stirred at room temperature (about 25°C.) for 18 hrs. The solvents are then removed by evaporation under reduced pressure and the resulting residue is dissolved in methylene chloride and chromatographed over silica gel. Elution with 5,10 and 20% ethyl acetate in cyclohexane and evaporation of the eluate fractions gives a residue comprising methyl 2,6-dimethyl-2,5-undecadienoate.

Workup

  1. additionA mixture of 5.0 g
  2. temperatureunder reflux for 12 hrs
  3. customat 25°C., giving a red solution
  4. stirringthe mixture is stirred at room temperature (about 25°C.) for 18 hrs
  5. customThe solvents are then removed by evaporation under reduced pressure
  6. dissolutionthe resulting residue is dissolved in methylene chloride
  7. customchromatographed over silica gel
  8. washElution
  9. customwith 5,10 and 20% ethyl acetate in cyclohexane and evaporation of the eluate fractions

Sources & evidence

ORD record
ord-0af8c3e2cdeb4021bba3c57c2486297f
Source dataset
uspto-grants-1976_04
Patent number
US03953499

Reaction notes

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