Diethyl Oxalate → Ethyl 6-dimethylamino-2,4-dioxo-5-phenyl-5-hexenoate

HRID 1902663Notes

Reaction equation

HRID 1902663 reaction equation
[O-]CC.[Na+].[H-].[Na+].[CH3:7][N:8]([CH3:20])[CH:9]=[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11](=[O:13])[CH3:12].[C:21](OCC)(=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CCOCC.C(OCC)(=O)C.O.C(O)(=O)C.C(O)C>[CH3:20][N:8]([CH3:7])[CH:9]=[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11](=[O:13])[CH2:12][C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

10

Reactant 4

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 14883693-Buten-2-one, 4-(dimethylamino)-3-phenyl-HCID 2723922Sodium ethoxide2×

Product 1

HCID 54311792Ethyl 6-dimethylamino-2,4-dioxo-5-phenyl-5-hexenoate

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of sodium ethoxide was prepared by addition of ethanol (1.6 ml) to a stirred suspension of sodium hydride (1.3 g 50% dispersion, washed with petroleum spirit 40°-60° C.) in ether (50 ml) under nitrogen. A solution of 4-dimethylamino-3-phenyl-3-buten-2-one (4.8 g) and diethyl oxalate (5.2 ml) in ether (50 ml) was added to the stirred sodium ethoxide suspension at 5° to 10° C. and the resulting clear solution was stirred for 2 hours at room temperature, then cooled and treated with glacial acetic acid (2.5 ml) and water (50 ml). Ethyl acetate was added to dissolve the solid which formed and the solvent layer was washed with water, dried, and evaporated. The solid residue was recrystallised from ethyl acetate-petroleum spirit (60°-80° C.) to give ethyl 6-dimethylamino-2,4-dioxo-5-phenyl-5-hexenoate (mp 110° C.).

Workup

  1. temperaturecooled
  2. dissolutionto dissolve the solid which
  3. customformed
  4. washthe solvent layer was washed with water
  5. customdried
  6. customevaporated
  7. customThe solid residue was recrystallised from ethyl acetate-petroleum spirit (60°-80° C.)

Sources & evidence

ORD record
ord-c5b4261b54e84bae961ddbe894683a3b
Source dataset
uspto-grants-1982_12
Patent number
US04364956

Reaction notes

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