Hydrochloric Acid → HCID 10933663, compound

HRID 890638Notes

Reaction equation

HRID 890638 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20].Cl>O1CCCC1>[CH2:20]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 759066-Bromo-1-hexene

Product 1

HCID 10933663HCID 10933663, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 120 ml of dry tetrahydrofuran (THF) was added 4.9 g of 60% sodium hydride, and 29.5 g of diethyl malonate was added dropwise with stirring under ice-cooling. After addition, stirring was continued for 15 minutes, and then 10 g of 6-bromo-1-hexen was added to the mixture and heated to reflux for 21 hours. The reaction solution was cooled, poured into ice-cold water, neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=20:1) to provide 14.5 g of the objective compound as yellowish oil.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. additionAfter addition
  4. stirringstirring
  5. temperatureheated
  6. temperatureto reflux for 21 hours
  7. temperatureThe reaction solution was cooled
  8. additionpoured into ice-cold water
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated
  13. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-cd7ea94b29794c74a9618231555a8bb6
Source dataset
uspto-grants-2006_02
Patent number
US06998412B2

Reaction notes

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