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

HRID 1902663ノート

反応式

HRID 1902663 の反応式
[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]

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.).

後処理

  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.)

出典と根拠

ORDレコード
ord-c5b4261b54e84bae961ddbe894683a3b
出典データセット
uspto-grants-1982_12
特許番号
US04364956

反応ノート

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