Ethyl Acetate → HCID 66618902, compound

HRID 406326Notes

Reaction equation

HRID 406326 reaction equation
[H-].[Na+].[CH:3]([C:6]1[C:7]([O:18][CH3:19])=[CH:8][C:9]([CH3:17])=[C:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:11]=1)([CH3:5])[CH3:4].[Cl:20][CH2:21][CH2:22][CH2:23]I.C(OCC)(=O)C>CN(C)C=O>[Cl:20][CH2:21][CH2:22][CH2:23][CH:12]([C:10]1[CH:11]=[C:6]([CH:3]([CH3:5])[CH3:4])[C:7]([O:18][CH3:19])=[CH:8][C:9]=1[CH3:17])[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 70224727HCID 70224727, compound

Product 1

HCID 66618902HCID 66618902, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

60% sodium hydride (928 mg) was suspended in anhydrous N,N-dimethylformamide (50 mL). A solution of methyl (5-isopropyl-4-methoxy-2-methylphenyl)acetate (5 g) in anhydrous N,N-dimethylformamide (30 mL) was added in a nitrogen atmosphere, so that the internal temperature was maintained at 4 to 6° C. After stirring at the same temperature for five minutes, 1-chloro-3-iodopropane (4.5 mL) was added so that the internal temperature was maintained at 4 to 6° C. After addition of the reagent, the mixture was brought back to room temperature and stirred for four hours. Ethyl acetate was added to the reaction solution, followed by washing with water. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (7.7 g). The property values of the compound are as follows.

Workup

  1. temperaturewas maintained at 4 to 6° C
  2. additionAfter addition of the reagent
  3. customwas brought back to room temperature
  4. stirringstirred for four hours
  5. washby washing with water
  6. washThe resulting organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe drying agent was separated by filtration
  9. concentrationthe organic layer was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-067a3150637647ae87f7370b93e0abbb
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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