Acetic Acid → 4,4-Diacetyl-5-(ethoxycarbonyl)-heptanedioic acid diethyl ester

HRID 1375113ノート

反応式

HRID 1375113 の反応式
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][CH:7]([C:11](=[O:13])[CH3:12])[C:8](=[O:10])[CH3:9])[CH3:2].[CH2:15]([O:17][C:18](=[O:26])/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:16].N12CCCN=C1CCCCC2.C(O)(=O)C>N12CCCN=C1CCCCC2.C(OCC)C>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]([C:8](=[O:10])[CH3:9])([C:11](=[O:13])[CH3:12])[CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:26])[CH3:2]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 638144Diethyl fumarateHCID 2733934Hexanoic acid, 4-acetyl-5-oxo-, ethyl ester

生成物 1

HCID 587849534,4-Diacetyl-5-(ethoxycarbonyl)-heptanedioic acid diethyl ester収率 53.6%

試薬・触媒・溶媒 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene触媒HCID 3283Diethyl Ether溶媒

実験手順

25.7 g of 4-acetyl-5-oxohexanoic acid ethyl ester and 0.3 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene were mixed, and 35 g of fumaric acid diethyl ester was added at room temperature over 40 minutes. After stirring for 24 hours, the amount of 1,8-diazabicyclo-[5.4.0]-undec-7-ene was doubled and stirring continued until conversion was complete. 0.5 g of acetic acid and 50 ml of diethyl ether were added, and the solution was extracted with an aqueous potassium carbonate solution and water. Fractional distillation of the dry organic layer yielded 25.6 g of 4,4-diacetyl-5-(ethoxycarbonyl)-heptanedioic acid diethyl ester (boiling point: 170° C./0.002 mbar; purity: 93%; colorless). Content of the active structural element C3O2: 18%.

後処理

  1. stirringstirring
  2. extractionthe solution was extracted with an aqueous potassium carbonate solution and water
  3. distillationFractional distillation of the dry organic layer

出典と根拠

ORDレコード
ord-43fcb3f4a3f94e9d8d73a58231cdb343
出典データセット
uspto-grants-2007_01
特許番号
US07166648B2

反応ノート

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