Methyl vinyl ketone → 2-Butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone

HRID 7847

반응식

HRID 7847 반응식
[CH:1]([C:3]([CH3:5])=[O:4])=[CH2:2].N12CCCN=C1CCCCC2.[CH2:17]([CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:31][CH3:32])[C:27]=2[CH3:30])[C:22]1=[O:33])[CH2:18][CH2:19][CH3:20]>O1CCCC1.CCOCC>[CH2:17]([C:21]1([CH2:2][CH2:1][C:3](=[O:4])[CH3:5])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:31][CH3:32])[C:27]=2[CH3:30])[C:22]1=[O:33])[CH2:18][CH2:19][CH3:20]

참가 물질

6

반응물 3

HCID 6570Methyl vinyl ketoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219908832-Butyl-5-methoxy-4-methyl-1-indanone

생성물 1

HCID 219908922-Butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone수율 81.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

Methyl vinyl ketone (MVK, 0.49 mL, 5.9 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.12 mL, 0.8 mmol) were added to a solution of impure 2-butyl-5-methoxy-4-methyl-1-indanone (0.90 g, 3.9 mmol) in anhydrous tetrahydrofuran (THF, 3.9 mL). The resulting solution was stirred at room temperature for 30 hours, then diluted with Et2O (50 mL), washed with water (20 mL), 1N HCl (20 mL), and brine (20 mL), dried over MgSO4, filtered, and evaporated under vacuum to an amber oil (1.23 g). The crude product was purified by chromatography on EM silica gel 60 (230-400 mesh, 125 mL dry, packed under 4:1 hexanes-EtOAc). The column was eluted with 4:1 hexanes-EtOAc, collecting 25 mL fractions. Fractions 14-27 gave a 93:2:5 mixture (0.96 g) of 2-butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone, the 6-methyl isomer, and the desmethyl product. This material was used in the next step.

후처리

  1. washwashed with water (20 mL), 1N HCl (20 mL), and brine (20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum to an amber oil (1.23 g)
  5. customThe crude product was purified by chromatography on EM silica gel 60 (230-400 mesh, 125 mL dry, packed under 4:1 hexanes-EtOAc)
  6. washThe column was eluted with 4:1 hexanes-EtOAc
  7. customcollecting 25 mL fractions

출처 및 근거

ORD 기록
ord-2a4993889ca6480cb0bfdfaca22cc970
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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