Diazomethane → HCID 10975696, compound

HRID 1589902Notes

Reaction equation

HRID 1589902 reaction equation
[N+](=[CH2:3])=[N-].[O:4]=[C:5]1[CH2:10][CH:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH2:6]1>CCOCC>[O:4]=[C:5]1[CH2:10][CH:9]([C:11]([O:13][CH3:3])=[O:12])[CH:8]=[CH:7][CH2:6]1

Participants

4

Reactant 2

HCID 9550Diazomethane2×HCID 10964594HCID 10964594, compound

Product 1

HCID 10975696HCID 10975696, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.7M diazomethane in ether was slowly added to a solution of 6.0 g (42.8 mmol) of 5-oxocyclohex-2-ene-1-carboxylic acid in 100 mL of ether at 0 degrees centigrade, with swirling. The addition of diazomethane was continued until the bubbling ceased and a yellow color persisted. The solution was treated with a rapid stream of nitrogen until the yellow color was discharged. The solvent was removed by evaporation. Benzene (100 mL) was added and evaporated at room temperature using an aspirator. The residue was placed on a vacuum line for 2 hours to produce 6.5 g (42.4 mmol, 99 percent) of methyl 5-oxocyclohex-2-ene-1-carboxylate (oil).

Workup

  1. additionThe solution was treated with a rapid stream of nitrogen until the yellow color
  2. customThe solvent was removed by evaporation
  3. additionBenzene (100 mL) was added
  4. customevaporated at room temperature

Sources & evidence

ORD record
ord-8dc1a112e17f4398a2a21f8b5028150c
Source dataset
uspto-grants-1993_04
Patent number
US05200513

Reaction notes

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