Hydrochloric Acid → HCID 10933663, compound

HRID 1794229Notes

Reaction equation

HRID 1794229 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, compound

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

Sources & evidence

ORD record
ord-9834fba732f54408891dc0c3f8f243c7
Source dataset
uspto-grants-2006_04
Patent number
US07022723B2

Reaction notes

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