Hydrochloric Acid → HCID 49781174, compound

HRID 1642042Notes

Reaction equation

HRID 1642042 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[C:12]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13]1.Cl>O>[F:3][C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[C:13]2/[C:12](=[O:17])[CH2:16][CH2:15][CH2:14]/2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8452CyclopentanoneHCID 14797Potassium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 49781174HCID 49781174, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of KOH (1.5 g, 26.7 mMol) in water (27 mL) was added to 4-fluoro-benzaldehyde Compound 3a (7.45 g, 60.0 mMol) and cyclopentanone Compound 1a (5.0 g, 59.4 mMol). The mixture was heated to 65° C. and stirred for 24 hrs at 65° C. The reaction mixture was allowed to cool to ambient temperature, acidified to pH 3 using 1N HCl and extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over Na2SO4, then filtered and concentrated. The resulting residue was purified on a silica gel column (using 5% EtOAc/Hexane) to give (2E)-2-(4-fluoro-benzylidene)-cyclopentanone Compound 3b (2.60 g, 13.7 mMol).

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified on a silica gel column (using 5% EtOAc/Hexane)

Sources & evidence

ORD record
ord-11ca40f82d0841c4b769a3fc891be7e4
Source dataset
uspto-grants-2012_02
Patent number
US08119621B2

Reaction notes

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