1,4-Dibromobutane → 1-acetyl-N-benzylcyclopentane carboxamide

HRID 1477941

반응식

HRID 1477941 반응식
[CH2:1]([NH:8][C:9](=[O:14])[CH2:10][C:11](=[O:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][CH2:24][CH2:25]Br>CN(C=O)C>[C:11]([C:10]1([C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:14])[CH2:25][CH2:24][CH2:23][CH2:22]1)(=[O:13])[CH3:12]

참가 물질

5

반응물 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 70159Acetoacetobenzylamide

생성물 1

HCID 1183901231-acetyl-N-benzylcyclopentane carboxamide수율 54.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-benzyl-3-oxobutanamide (100.00 g, 522.93 mmol), K2CO3 (216.50 g, 1568.79 mmol) in DMF (1 L) was added 1,4-dibromobutane (169.36 g, 784.4 mmol) dropwise at rt. After addition, the reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was added water (500 mL) and extracted with EtOAc (500 mL×3). The combined organic phases were washed with brine (500 mL×3), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/8) to give the product as a white solid (69.50 g, 54%).

후처리

  1. additionAfter addition
  2. concentrationconcentrated in vacuo
  3. additionThe residue was added water (500 mL)
  4. extractionextracted with EtOAc (500 mL×3)
  5. washThe combined organic phases were washed with brine (500 mL×3)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/8)

출처 및 근거

ORD 기록
ord-71f4774d367f43dabb4a5bfde6710acd
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403801B2

연결된 노트

불러오는 중…