Sodium hydride → HCID 86670684, compound

HRID 1752015Notes

Reaction equation

HRID 1752015 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8][CH:7]([CH3:10])[C:6]1=[O:11])=[O:4].[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:9][CH2:8][C:7]([CH2:17][C:16]([Cl:19])=[CH2:15])([CH3:10])[C:6]1=[O:11])=[O:4]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 11482916115851-54-22×

Product 1

HCID 86670684HCID 86670684, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1-(4-chlorobenzyl)-3-methyl-2-oxocyclopentane carboxylic acid methyl ester (Compound (XII), R1=CH3, R2=CH3) (4.0 g, 14.2 mmol) was dissolved in DMF (20 ml), sodium hydride (0.63 g (ca. 60% in mineral oil), 15.8 mmol) was added, and the solution was heated to about 60 degrees C., and then cooled with ice. 2,3-Cichloropropene (1.89 g, 17.0 mmol) was added, the ice bath was removed, stirring was conducted at room temperature for 5 hours, and then stirring was conducted at about 60 degrees C. for 1 hour. To the reaction solution, water (50 ml) was added, extraction with ethyl acetate (80 ml×2) was conducted, and then the organic layer was washed with saturated brine (50 ml), and then dried over anhydrous sodium sulfate, and concentrated. A silica gel column (eluent; hexane:ethyl acetate=10:1) was employed for purification to obtain the desired substance.

Workup

  1. temperature, and then cooled with ice
  2. addition2,3-Cichloropropene (1.89 g, 17.0 mmol) was added
  3. customthe ice bath was removed
  4. stirringstirring
  5. customwas conducted at about 60 degrees C
  6. waitfor 1 hour
  7. additionTo the reaction solution, water (50 ml) was added
  8. extractionextraction with ethyl acetate (80 ml×2)
  9. washthe organic layer was washed with saturated brine (50 ml)
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customA silica gel column (eluent; hexane:ethyl acetate=10:1) was employed for purification
  13. customto obtain the desired substance

Sources & evidence

ORD record
ord-de71dd17408041e9a7d1ae3c5f443955
Source dataset
uspto-grants-2015_10
Patent number
US09162966B2

Reaction notes

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