1-Penten-3-one → 2-Butyl-5-methoxy-4-methyl-2-(3-oxopentyl)-1-indanone

HRID 7851

反応式

HRID 7851 の反応式
[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[C:11]=2[CH3:14])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].[CH:18]([C:20]([CH2:22][CH3:23])=[O:21])=[CH2:19].N12CCCN=C1CCCCC2>O1CCCC1.CCOC(C)=O>[CH2:1]([C:5]1([CH2:19][CH2:18][C:20](=[O:21])[CH2:22][CH3:23])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[C:11]=2[CH3:14])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 3

HCID 153941-Penten-3-one2 回HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2 回HCID 219908832-Butyl-5-methoxy-4-methyl-1-indanone

生成物 1

HCID 219909302-Butyl-5-methoxy-4-methyl-2-(3-oxopentyl)-1-indanone

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A solution of 2-butyl-5-methoxy-4-methyl-1-indanone (100 mg, 0.43 mmol) in tetrahydrofuran (0.43 mL) was treated with ethyl vinyl ketone (EVK, 0.064 mL, 0.646 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.013 mL, 0.086 mmol). The resulting solution was stirred under a nitrogen atmosphere and heated in an oil bath at 60° C. After 24 hour, more EVK (0.064 mL) and DBU (0.013 mL) were added and the solution was heated an additional 24 hours at 60° C. The reaction mixture was diluted with EtOAc (10 mL) and washed with water (10 mL) containing 2N HCl (1 mL). The organic phase was washed with brine (5 mL), dried over MgSO4, filtered, and evaporated under vacuum to provide crude 2-butyl-5-methoxy-4-methyl-2-(3-oxopentyl)-1-indanone.

後処理

  1. temperaturethe solution was heated an additional 24 hours at 60° C
  2. washwashed with water (10 mL)
  3. additioncontaining 2N HCl (1 mL)
  4. washThe organic phase was washed with brine (5 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum

出典と根拠

ORDレコード
ord-ab9cbb76965644d483935f81bfcf3531
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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