1-Chloro-3-methyl-2-butene → HCID 53672322, compound

HRID 1957548Notes

Reaction equation

HRID 1957548 reaction equation
[CH2:1]([C:4]1[C:13](OCC=C)=CC=C2[C:5]=1CCC(=O)N2)[CH:2]=C.[CH2:19]([C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][CH2:27][C:28](=[O:32])[NH:29]2)=[CH:24][C:23]=1[O:33][CH2:34][CH:35]=[CH2:36])[CH:20]=[CH2:21].[H-].[Na+].[H][H].C(Cl)C=C(C)C>CN(C)C=O.O>[CH2:34]([O:33][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:22]=1[CH:19]=[CH:20][CH3:21])[N:29]([CH2:2][CH:1]=[C:4]([CH3:13])[CH3:5])[C:28](=[O:32])[CH2:27][CH2:26]2)[CH:35]=[CH2:36]

Participants

8

Reactant 5

HCID 104291-Chloro-3-methyl-2-buteneHCID 24758Sodium hydrideHCID 19068037HCID 19068037, compoundHCID 19068063HCID 19068063, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53672322HCID 53672322, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

80 Grams of the mixture of 5-allyl-6-allyloxy-3,4-dihydro-2(1H)-quinolinone and 7-allyl-6-allyloxy-3,4-dihydro-2(1H)-quinolinone obtained in Example 16 was dissolved in 300 ml of dimethylformamide, then 15 g of 60% oily sodium hydride was added little by little thereto at room temperature and stirred at 25° to 40° C. until generation of hydrogen gas was ceased. After the reaction mixture was cooled to room temperature, 35 g of prenyl chloride was added thereto and stirred at 50° C. for 2 hours, further stirred at room temperature for 8 hours. After finished the reaction, the dimethylformamide was removed by distillation under reduced pressure to obtain the residue. To the residue was added water and extracted with ethyl acetate. The extract was washed with water and an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration, and the filtrate was concentrated to obtain pale yellow oily product. This oily product was subjected to separation and purification by means of a silica gel flush chromatography, by using a mixed solvent of ethyl acetate:n-hexane (1:10 to 1:2) as the eluent, there was obtained 29 g (28.3%) of 6-allyloxy-3,4-dihydro-1-prenyl-7-(1-propenyl)-2(1H)-quinolinone.

Workup

  1. stirringfurther stirred at room temperature for 8 hours
  2. customthe reaction
  3. customthe dimethylformamide was removed by distillation under reduced pressure
  4. customto obtain the residue
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialan aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate
  8. customThe magnesium sulfate was removed by filtration
  9. concentrationthe filtrate was concentrated
  10. customto obtain pale yellow oily product
  11. customThis oily product was subjected to separation and purification by means of a silica gel
  12. customflush chromatography

Sources & evidence

ORD record
ord-83ef136ef2974aa0a1d6212b1e41aeb3
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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