Hydrochloric Acid → HCID 86595849, compound

HRID 857217Notes

Reaction equation

HRID 857217 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[CH:15]([CH3:31])[CH2:16][CH2:17][CH2:18][C:19]1[N:20]=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:22][C:23]=1[CH3:24].Cl>O1CCCC1>[CH3:24][C:23]1[O:22][C:21]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:20][C:19]=1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:31][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 21866693HCID 21866693, compound

Product 1

HCID 86595849HCID 86595849, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 35 ml of dry tetrahydrofuran, 650 mg of 60% sodium hydride was added, and 3.9 g of diethyl malonate was added dropwise with stirring under ice-cooling. After the stirring was continued for 10 minutes, 4-(4-bromopentyl)-5-methyl-2-phenyloxazol (2.5 g) was added. The mixture was stirred for 10 minutes at room temperature and then heated to reflux for 12 hours. The reaction solution was poured into ice-cold water, neutralized with dilute hydrochloric acid and then 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=10:1) to provide 2.75 g of the objective compound as colorless oil.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 10 minutes at room temperature
  3. temperatureheated
  4. temperatureto reflux for 12 hours
  5. additionThe reaction solution was poured into ice-cold water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d7dbf2a1e5f441bbabd648c4ff64545a
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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