Methanol → HCID 14373508, compound

HRID 2291637Notes

Reaction equation

HRID 2291637 reaction equation
[N+](=[CH:3][C:4](=O)[CH2:5][CH2:6][CH:7]1[O:11][C:10](=[O:12])[C:9]([O:13][CH3:14])=[C:8]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N-].C([O:24][CH2:25]C)C.C[OH:28]>C(N(CC)CC)C.C([O-])(=O)C1C=CC=CC=1.[Ag+]>[CH3:14][O:13][C:9]1[C:10](=[O:12])[O:11][CH:7]([CH2:6][CH2:5][CH2:4][C:3]([O:24][CH3:25])=[O:28])[C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 3283Diethyl EtherHCID 54256923HCID 54256923, compound

Product 1

HCID 14373508HCID 14373508, compound

Reagents, catalysts & solvents 2

HCID 164649Silver benzoateCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 5-(4-diazo-3-oxobutyl)-3-methoxy-4-phenyl-2(5H)-furanone (100 mg) in methanol (2 ml) was added dropwise a solution of silver benzoate (9.6 mg) in triethylamine (0.2 ml) over a period of 10 minutes at 0° C. with stirring and the mixture was stirred for 30 minutes at ambient temperature. The reaction mixture was filtered off and the filtrate was condensed and dituted with diethyl ether. The ethereal solution was washed with lN hydrochloric acid, water and brine successively and dried. Evaporation of the solvent gave methyl 4-(4-methoxy-5-oxo-3-phenyl-2,5-dihydro2-furyl)butyrate (100 mg) as an oil.

Workup

  1. stirringthe mixture was stirred for 30 minutes at ambient temperature
  2. filtrationThe reaction mixture was filtered off
  3. customcondensed
  4. washThe ethereal solution was washed with lN hydrochloric acid, water and brine successively
  5. customdried
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7aa7d8f4015346dfa94d11640261bf8b
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

Loading…