HCID 13632645, compound → HCID 13632647, compound

HRID 280388Notes

Reaction equation

HRID 280388 reaction equation
[C:1]([C:3]1([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH:4]1[C:6]([CH3:8])=[CH2:7])#[N:2]>C1(C)C=CC=CC=1>[C:1]([C:3]1([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH:4]=[C:6]([CH3:7])[CH2:8]1)#[N:2]

Participants

3

Reactant 1

HCID 13632645HCID 13632645, compound

Product 1

HCID 13632647HCID 13632647, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 41.0 g of methyl 1-cyano-2-(1-methylethenyl)cyclopropane-1-carboxylate in 300 ml of toluene was passed through a pyrolysis column packed with glass helices and held at 425° C. A nitrogen flow rate was chosen which resulted in a contact time of 1-2 sec and the pyrolysate was collected in a dry ice-isopropyl alcohol cooled flask. The toluene solution was washed with 300 ml of saturated aqueous sodium bicarbonate and 300 ml of saturated sodium chloride solution, dried (MgSO4), and concentrated in vacuo to leave 32.5 g of brown oil. Distillation of the oil gave 30.4 g of the desired product as a yellow oil: b.p. 75°-100° (0.05 mm Hg).

Workup

  1. customheld at 425° C
  2. customresulted in a contact time of 1-2 sec
  3. customthe pyrolysate was collected in a dry ice-isopropyl alcohol cooled flask
  4. washThe toluene solution was washed with 300 ml of saturated aqueous sodium bicarbonate and 300 ml of saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71702b1f4cbf458c93d5e78e85d4d092
Source dataset
uspto-grants-1986_05
Patent number
US04588821

Reaction notes

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