Ethyl diazoacetate → HCID 20344530, compound

HRID 2049831Notes

Reaction equation

HRID 2049831 reaction equation
[C:1]1([S:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N-]>C1CCCCC1>[C:1]1([S:7][CH:8]2[CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9]2([CH3:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 12308536Benzene, [(2-methyl-1-propenyl)thio]-

Product 1

HCID 20344530HCID 20344530, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent2×

Procedure

To a mixture of 1.94 g (11.8 mmol) of 2-methyl-1-propenyl phenyl sulfide, 200 mg anhydrous cupric sulfate and 10 ml cyclohexane heated under reflux is added, dropwise and with stirring over a 7 hr period, a solution of 6.58 g (58 mmol) of ethyl diazoacetate in 40 ml cyclohexane. After addition is complete, refluxing and stirring is continued for an additional 2 hr, and then the reaction mixture is filtered, dried and solvent is removed in vacuo to give ethyl 3-phenylthio-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. additionis added
  4. additionAfter addition
  5. temperaturerefluxing
  6. stirringstirring
  7. waitis continued for an additional 2 hr
  8. filtrationthe reaction mixture is filtered
  9. customdried
  10. customsolvent is removed in vacuo

Sources & evidence

ORD record
ord-cb4e2a4f75304cb3b5571424f7f854e2
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

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