Sodium hydride → 6-allyloxy-3,4-dihydro-1-prenyl-2-(1H)-quinolinone

HRID 1957534노트

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HRID 1957534 반응식
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)[CH:2]=[CH2:3].[H-].[Na+].[H][H].[CH2:20](Br)[CH:21]=[C:22]([CH3:24])[CH3:23]>CN(C)C=O.O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[C:10](=[O:15])[CH2:9][CH2:8]2)[CH:2]=[CH2:3]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-HCID 190680326-(allyloxy)-3,4-dihydroquinolin-2(1H)-oneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 190679146-allyloxy-3,4-dihydro-1-prenyl-2-(1H)-quinolinone수율 59.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

10.2 Grams of 6-allyloxy-3,4-dihydro-2(1H)-quinolinone was dissolved in 100 ml of dimethyl-formamide (DMF), then at room temperature, 2.2 g of 60% oily sodium hydride was added little by little thereto, and the reaction mixture was stirred at 25° to 40° C. until generation of hydrogen was stopped. The reaction mixture was cooled to room temperature, 9.1 g of prenyl bromide was added thereto and stirred at room temperature for 8 hours. After the reaction was completed, water was added, and the reaction mixture was extracted with methylene chloride. The methylene chloride extract was washed with water and an aqueous solution saturated with sodium chloride in this order, then thus washed extract was dried with anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration and concentrated. Thus obtained oily residue was subjected to refining and separating by means of a silica gel flush column chromatography by using mixed solvent of ethyl acetate:n-hexane (1:10 to 1:2) as an eluent to obtain 10.2 g (59.7%) of 6-allyloxy-3,4-dihydro-1-prenyl-2-(1H)-quinolinone.

후처리

  1. extractionthe reaction mixture was extracted with methylene chloride
  2. extractionThe methylene chloride extract
  3. washwas washed with water
  4. washan aqueous solution saturated with sodium chloride in this order, then thus washed
  5. extractionextract
  6. dry with materialwas dried with anhydrous magnesium sulfate
  7. customMagnesium sulfate was removed by filtration
  8. concentrationconcentrated
  9. customseparating by means of a silica gel
  10. customflush column chromatography
  11. additionby using mixed solvent of ethyl acetate:n-hexane (1:10 to 1:2) as an eluent

출처 및 근거

ORD 기록
ord-c2641e0d106e4d17a438014d26a11dec
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05786367

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