Sodium hydride → HCID 17958600, compound

HRID 2243298Notes

Reaction equation

HRID 2243298 reaction equation
[H-].[Na+].[C:3]([O:12][CH2:13][CH:14]=[CH2:15])(=[O:11])[CH2:4][C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6].Br[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]>O1CCOCC1>[CH:4]([C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])([C:3]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79557Methyl 5-bromovalerateHCID 228227Diallyl malonate

Product 1

HCID 17958600HCID 17958600, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1.50 g (52.22 mmol) of sodium hydride were added carefully to a solution of 2.00 g (69.62 mmol) of diallyl malonate in 700 ml of dioxane. After the evolution of gas had ended, the mixture was stirred at room temperature for 20 min, and a solution of 7.00 g (34.81 mmol) of methyl 5-bromovalerate in 120 ml of dioxane was added dropwise. The solution was stirred at 110° C. for 16 h. The resulting precipitate was filtered off, the solvent was removed and the residue was taken up in water. The mixture was extracted with diethyl ether, the combined organic phases were dried over Na2SO4 and the solvent was removed. The product was purified chromato-graphically (silica gel, cylcohexane/ethyl acetate 10:1).

Workup

  1. stirringThe solution was stirred at 110° C. for 16 h
  2. filtrationThe resulting precipitate was filtered off
  3. customthe solvent was removed
  4. extractionThe mixture was extracted with diethyl ether
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. customthe solvent was removed
  7. customThe product was purified chromato-graphically (silica gel, cylcohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-1aed4dc9ee88453f9b24aa8e2c44155e
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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