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

HRID 7851

반응식

HRID 7851 반응식
[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]

참가 물질

6

반응물 3

HCID 153941-Penten-3-one2회HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2회HCID 219908832-Butyl-5-methoxy-4-methyl-1-indanone

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab9cbb76965644d483935f81bfcf3531
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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