Diazomethane → HCID 54256923, compound

HRID 2291624Notes

Reaction equation

HRID 2291624 reaction equation
[CH3:1][O:2][C:3]1[C:7](=[O:8])[O:6][CH:5]([CH2:9][CH2:10][C:11]([OH:13])=O)[C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N+:20](=[CH2:22])=[N-:21]>S(Cl)(Cl)=O.C(Cl)Cl.C(OCC)C>[N+:20](=[CH:22][C:11](=[O:13])[CH2:10][CH2:9][CH:5]1[O:6][C:7](=[O:8])[C:3]([O:2][CH3:1])=[C:4]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N-:21]

Participants

6

Reactant 2

HCID 9550DiazomethaneHCID 13832260HCID 13832260, compound

Product 1

HCID 54256923HCID 54256923, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-(4-methoxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionic acid (500 mg) in thionyl chloride (2 ml) was heated at 70° C. with stirring for 1 hour. After cooling, the solvent was removed under the reduced pressure to give a residue which was taken up in methylene chloride. To this solution was added dropwise a solution of diazomethane in diethyl ether. The solvent was removed under the reduced pressure to give 5-(4-diazo-3-oxobutyl)-3-methoxy-4-phenyl-2(5H)furanone (465 mg) which was recrystallized from diisopropyl ether.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed under the reduced pressure
  3. customto give a residue which
  4. customThe solvent was removed under the reduced pressure

Sources & evidence

ORD record
ord-578bd98a5a054174824ff9d6a26e3be2
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

Loading…