Diethyl Oxalate → HCID 13156241, compound

HRID 851689Notes

Reaction equation

HRID 851689 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[N:14]([C:15]=2[C:16]([CH3:18])=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:21](OCC)(=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[C:9]3[N:14]([C:15]=2[C:16](=[O:17])[CH2:18][C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 3766827HCID 3766827, compound

Product 1

HCID 13156241HCID 13156241, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 25.7 g of methyl 2-phenyl-3-indolizinyl ketone in 360 ml of benzene were added 8.3 g of 50% sodium hydride and 28.2 g of diethyl oxalate, and the mixture was heated at 60° C. for 30 minutes. After cooling, the benzene was distilled off. To the residue was added 200 ml of water and the aqueous solution was acidified with acetic acid. Crystals precipitated were filtered off and washed with water, and then recerystallized from ethanol to give 30 g of ethyl 4-(2-phenyl-3-indolizinyl)-2,4-dioxobutyrate, melting at 100°-102° C.

Workup

  1. temperatureAfter cooling
  2. distillationthe benzene was distilled off
  3. additionTo the residue was added 200 ml of water
  4. customCrystals precipitated
  5. filtrationwere filtered off
  6. washwashed with water

Sources & evidence

ORD record
ord-b15ca260e0a74a099a8e7cc352d5a89b
Source dataset
uspto-grants-1983_05
Patent number
US04386092

Reaction notes

Loading…