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

HRID 1902663노트

반응식

HRID 1902663 반응식
[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]

참가 물질

10

반응물 4

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 14883693-Buten-2-one, 4-(dimethylamino)-3-phenyl-HCID 2723922Sodium ethoxide2회

생성물 1

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

시약·촉매·용매 5

HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.).

후처리

  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.)

출처 및 근거

ORD 기록
ord-c5b4261b54e84bae961ddbe894683a3b
출처 데이터셋
uspto-grants-1982_12
특허 번호
US04364956

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