2-Pyrrolidone → Piperyline

HRID 631939노트

반응식

HRID 631939 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:29]1[CH2:33][CH2:32][CH2:31][C:30]1=O>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8](/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:16])=[CH:9][C:4]=2[O:3][CH2:2]1

참가 물질

5

반응물 3

HCID 120252-PyrrolidoneHCID 682631,1'-CarbonyldiimidazoleHCID 5370536Piperic acid

생성물 1

HCID 636537Piperyline수율 58.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoic acid (50 mg, 0.23 mmol) was dissolved in 1,1′-carbonyldiimidazole (56 mg, 0.34 mmol) in THF (1.5 mL), followed by stirring for 1 hour. Then, pyrrolidone (0.03 mL, 0.34 mmol) was added thereto, followed by stirring for 6 hours. Upon completion of the reaction, the experiment was completely terminated by addition of distilled water. EtOAc was added to the reaction product to separate an oil layer and a water layer from each other, followed by washing with a saturated solution of NaCl and then drying over anhydrous Na2SO4. The solvent was distilled under reduced pressure. The residue was purified by column chromatography using hexane/ethyl acetate (1/1) to give a target compound (36.1 mg, yield: 58.1%).

후처리

  1. stirringby stirring for 6 hours
  2. customUpon completion of the reaction
  3. customthe experiment was completely terminated by addition of distilled water
  4. additionEtOAc was added to the reaction product
  5. customto separate an oil layer
  6. washby washing with a saturated solution of NaCl
  7. dry with materialdrying over anhydrous Na2SO4
  8. distillationThe solvent was distilled under reduced pressure
  9. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-bbeb8677cd314d6896a1df4273ca3c52
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321751B2

반응 노트

불러오는 중…