Ethyl vinyl ether → HCID 57950908, compound

HRID 1039698Notes

Reaction equation

HRID 1039698 reaction equation
C([O:3][CH2:4][CH3:5])=C.[N+](=[CH:8][C:9]([O:11][CH2:12][CH3:13])=O)=[N-].[OH2:14].[OH-].[Li+:16]>C(Cl)Cl.O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:12]([O:11][CH:9]1[CH2:8][CH:5]1[C:4]([O-:14])=[O:3])[CH3:13].[Li+:16]

Participants

7

Reactant 3

HCID 8023Ethyl vinyl etherHCID 12192Ethyl diazoacetateHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 57950908HCID 57950908, compound

Reagents, catalysts & solvents 3

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

In a 250 mL RBF, ethyl vinyl ether (4.2 ml, 44 mmol) was dissolved in DCM (20 mL). Rhodium (II) acetate dimer (0.019 g, 0.044 mmol) was added as a green powder, and ethyl diazoacetate (0.91 ml, 8.8 mmol) was added as a solution in DCM (4 mL) to the reaction mixture. The mixture was stirred overnight and concentrated. The crude mixture was dissolved in MeOH (0.75 mL), and lithium hydroxide hydrate (0.014 g, 0.34 mmol) was added as a solution in water (0.75 mL). The reaction mixture was stirred overnight, then concentrated and the title compound was used without purification.

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude mixture was dissolved in MeOH (0.75 mL)
  3. stirringThe reaction mixture was stirred overnight
  4. concentrationconcentrated
  5. customthe title compound was used without purification

Sources & evidence

ORD record
ord-02159a91655c4ee4b133347c4c7276f6
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Reaction notes

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