1-Penten-3-one → 2-Butyl-5-methoxy-2-(3-oxo-pentyl)-1-indanone

HRID 7824

반응식

HRID 7824 반응식
[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].N12CCCN=C1CCCCC2.[CH:28]([C:30]([CH2:32][CH3:33])=[O:31])=[CH2:29]>O1CCCC1>[CH2:1]([C:5]1([CH2:29][CH2:28][C:30](=[O:31])[CH2:32][CH3:33])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 153941-Penten-3-oneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 120457522-Butyl-5-methoxy-1-indanone

생성물 1

HCID 219909272-Butyl-5-methoxy-2-(3-oxo-pentyl)-1-indanone수율 27.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of crude 2-butyl-5-methoxy-1-indanone (218 mg, 1 mmol) in tetrahydrofuran (THF, 2 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.030 mL, 0.2 mmol) and ethyl vinyl ketone (EVK, 0.200 mL, 2 mmol). The resulting solution was stirred under a nitrogen atmosphere at room temperature for 16 hours, followed by heating in an oil bath at 60° C. for 24 hours. Evaporation of the solvent under vacuum left a residue that was shown by NMR to be approximately a 1:1 mixture of starting material and product. The residue was purified by preparative layer chromatography on three 0.1×20×20 cm silica gel GF plates using 5% EtOAc in CH2Cl2 as developing solvent. The product band was eluted with EtOAc to provide 2-butyl-5-methoxy-2-(3-oxo-pentyl)-1-indanone (84 mg) as an oil.

후처리

  1. temperatureby heating in an oil bath at 60° C. for 24 hours
  2. customEvaporation of the solvent under vacuum
  3. waitleft a residue that
  4. additiona 1:1 mixture of starting material and product
  5. customThe residue was purified by preparative layer chromatography on three 0.1×20×20 cm silica gel GF plates
  6. washThe product band was eluted with EtOAc

출처 및 근거

ORD 기록
ord-a68e6a4e18124f449bac70683f3eb813
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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