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

HRID 7819

反応式

HRID 7819 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b2f702acf9204650b931ca10badf77fa
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

関連ノート

読み込み中…