Acetone → HCID 12094222, compound

HRID 275819Notes

Reaction equation

HRID 275819 reaction equation
C(O[CH:4](OCC)[CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)C)C.Cl.O.[OH-].[Na+].C[C:28](C)=[O:29]>>[CH:8]1([CH2:6][CH:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:4][CH:28]=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric Acid2×HCID 962WaterHCID 14798Sodium HydroxideHCID 22610116HCID 22610116, compound

Product 1

HCID 12094222HCID 12094222, compound

Procedure

2-Pyridyl-3-cyclohexyl-butyraldehyde diethyl acetal (650 mg) was dissolved in acetone (10 mL), treated with HCl (a solution of 2.5 mL concentrated HCl and 7.5 mL water) and the reaction was stirred at room temperature overnight. 1N sodium hydroxide (30 mL) was then added and the neutralized reaction mixture was extracted with ethyl acetate (2 times). The organic extracts were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide 4-cyclohexyl-3-(2-pyridyl)-butyraldehyde (480 mg) as an oil.

Workup

  1. extractionthe neutralized reaction mixture was extracted with ethyl acetate (2 times)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-35080e03399d4b00b9b1bc39ec3a88bb
Source dataset
uspto-grants-2002_03
Patent number
US06353008B1

Reaction notes

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