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

HRID 7847

反応式

HRID 7847 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2a4993889ca6480cb0bfdfaca22cc970
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

関連ノート

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