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

HRID 1375113노트

반응식

HRID 1375113 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene촉매HCID 3283Diethyl Ether용매

실험 절차

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%.

후처리

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

출처 및 근거

ORD 기록
ord-43fcb3f4a3f94e9d8d73a58231cdb343
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166648B2

반응 노트

불러오는 중…