Methyl vinyl ketone → 5-Methoxy-2-methyl-2-(3-oxo-butyl)-1-indanone

HRID 7819

반응식

HRID 7819 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]([CH3:13])[CH2:6]2.N12CCCN=C1CCCC[CH2:15]2.[CH:25]([C:27]([CH3:29])=[O:28])=C>O1CCCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]([CH3:15])([CH2:13][CH2:25][C:27](=[O:28])[CH3:29])[CH2:6]2

참가 물질

6

반응물 3

HCID 6570Methyl vinyl ketoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 122904905-Methoxy-2-methylindan-1-one

생성물 1

HCID 219909085-Methoxy-2-methyl-2-(3-oxo-butyl)-1-indanone수율 332.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 5-methoxy-2-methyl-1-indanone (0.5 g, 2.84 mmol) in anhydrous tetrahydrofuran (3 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (0.085 mL, 0.57 mmol) and methyl vinyl ketone (0.473 mL, 5.68 mmol). The resulting solution was placed under a nitrogen atmosphere and stirred at room temperature overnight. The mixture was diluted with EtOAc (25 mL), washed with 0.2N HCl (25 mL) and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum to a yellow oil (800 mg). The oil was dissolved in CH2Cl2 (10 mL) and the solution added to a small column of EM silica gel 60 (8 mL). The column was eluted with CH2Cl2 (30 ml) and the eluant evaporated under vacuum to afford 5-methoxy-2-methyl-2-(3-oxo-butyl)-1-indanone (467 mg) as an oil.

후처리

  1. washwashed with 0.2N HCl (25 mL) and brine (10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum to a yellow oil (800 mg)
  5. dissolutionThe oil was dissolved in CH2Cl2 (10 mL)
  6. additionthe solution added to a small column of EM silica gel 60 (8 mL)
  7. washThe column was eluted with CH2Cl2 (30 ml)
  8. customthe eluant evaporated under vacuum

출처 및 근거

ORD 기록
ord-b2f702acf9204650b931ca10badf77fa
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

연결된 노트

불러오는 중…