Ethyl vinyl ether → HCID 12731313, compound

HRID 1502421Notes

Reaction equation

HRID 1502421 reaction equation
[CH:1]([O:3][CH2:4][CH3:5])=[CH2:2].[N+](=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N-]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH2:1]([O:3][CH:4]1[CH2:5][CH:8]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2]

Participants

5

Reactant 2

HCID 8023Ethyl vinyl etherHCID 12192Ethyl diazoacetate

Product 1

HCID 12731313HCID 12731313, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl vinyl ether (4.5 mL, 47 mmol, 4.9 equiv.) and rhodium(II) acetate dimer (20.0 mg, 45.2 μmol, 4.8 mol %) in DCM (20 mL) at ambient temperature was treated with ethyl 2-diazoacetate (1.00 mL, 9.51 mmol) in 0.1 mL portions over 10 mins, allowing effervescence to subside between additions. The resulting green solution was stirred at ambient temperature for 2 h and concentrated in vacuo. The residue was dissolved in diethyl ether and washed with water, and with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford crude ethyl 2-ethoxycyclopropanecarboxylate as a golden yellow oil (1.36 g, 90%) which was used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in diethyl ether
  3. washwashed with water
  4. dry with materialwith brine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31e74505c4c4472dbb5666bcb872ae23
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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