Diazomethane → HCID 10975696, compound

HRID 234246Notes

Reaction equation

HRID 234246 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-ef95ceb2298248a083930a6338bed369
Source dataset
uspto-grants-1997_01
Patent number
US05594158

Reaction notes

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