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

HRID 7855

反応式

HRID 7855 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[Cl: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[Cl:14])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 3

HCID 153941-Penten-3-oneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219909172-Butyl-4-chloro-5-methoxy-1-indanone

生成物 1

HCID 219909112-Butyl-4-chloro-5-methoxy-2-(3-oxopentyl)-1-indanone収率 93.9%

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-4-chloro-5-methoxy-1-indanone (200 mg, 0.79 mmol) in anhydrous tetrahydrofuran (0.8 mL) was placed under a nitrogen atmosphere and treated with ethyl vinyl ketone (0.118 mL, 1.19 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (0.024 mL, 0.158 mmol). The resulting solution was stirred and heated in an oil bath at 60° C. for 47 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc (20 mL) and washed with water (20 mL) containing 2N HCl (2 mL). The organic phase was washed with brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum to provide crude 2-butyl-4-chloro-5-methoxy-2-(3-oxopentyl)-1-indanone (250 mg) as an oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (20 mL)
  3. additioncontaining 2N HCl (2 mL)
  4. washThe organic phase was washed with brine (10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum

出典と根拠

ORDレコード
ord-d1cb4b3435da4997860140228da64a57
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

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