Sodium hydride → HCID 19067911, compound

HRID 1957539Notes

Reaction equation

HRID 1957539 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(Br)C=C(C)C>CN(C)C=O.O>[CH2:19]([C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][CH2:27][C:28](=[O:32])[N:29]2[CH2:2][CH:1]=[C:4]([CH3:13])[CH3:5])=[CH:24][C:23]=1[O:33][CH2:34][CH:35]=[CH2:36])[CH:20]=[CH2:21]

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-HCID 19068037HCID 19068037, compoundHCID 19068063HCID 19068063, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19067911HCID 19067911, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

10.2 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 100 ml of dimethylformamide, then 2.2 g of 60% oily sodium hydride was added little by little, and stirred at 25° to 40° C. until generation of hydrogen gas was ceased. After the reaction mixture was cooled to room temperature, 9.1 g of prenyl bromide was added and stirred at room temperature for 8 hours. After the reaction was finished, water was added and extracted with methylene chloride, then the extract was washed with water and an aqueous solution saturated with sodium chloride in this order, and dried with anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration and the filtrate was concentrated. Thus obtained residual oily product was subjected to separation and purification by means of a silica gel flush column chromatography, there was obtained 10.2 g (59.7%) of 7-allyl-6-allyloxy-3,4-dihydro-1-prenyl-2(1H)-quinolinone.

Workup

  1. extractionextracted with methylene chloride
  2. washthe extract was washed with water
  3. dry with materialan aqueous solution saturated with sodium chloride in this order, and dried with anhydrous magnesium sulfate
  4. customThe magnesium sulfate was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customThus obtained residual oily product was subjected to separation and purification by means of a silica gel
  7. customflush column chromatography

Sources & evidence

ORD record
ord-1bf70af0091d4cb4abb37cdd93d64137
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

Loading…