Dimethylacetylene → Ethyl diazoacetate

HRID 1685063Notes

Reaction equation

HRID 1685063 reaction equation
[CH3:1][C:2]#[C:3][CH3:4].[N+:5](=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N-:6]>CCCCC>[CH3:1][C:2]1[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:4].[N+:5](=[CH:7][C:8]([O:10][CH2:3][CH3:4])=[O:9])=[N-:6]

Participants

5

Reactant 2

HCID 10419DimethylacetyleneHCID 12192Ethyl diazoacetate

Product 2

HCID 12192Ethyl diazoacetateHCID 12403518Ethyl 2,3-dimethylcycloprop-2-ene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Under a nitrogen atmosphere 2-butyn (9.50 g, 176 mmol) was cooled to 0° C. and Rh2(OAc)4 (195 mg) was added. To the resulting suspension was added slowly over a period of 4.5 hours ethyl diazoacetate (8.02 g, 70 mmol). The mixture was stirred for 30 minutes and pentane (30 mL) was added. The solids were removed by filtration over Celite and the filtrate was concentrated in vacuo to afford ethyl 2,3-dimethylcycloprop-2-enecarboxylate (below) as a mixture with ethyl diazoacetate.

Workup

  1. customThe solids were removed by filtration over Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-94df392798294dfc85ffa4b52727302d
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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