Water → HCID 54072301, compound

HRID 2085376Notes

Reaction equation

HRID 2085376 reaction equation
[C:1]([CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=O)[CH2:2][CH3:3].[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[F:25])[CH:20]=O.[OH2:26]>N1CCCCC1.C(O)(=O)C>[F:16][C:17]1[CH:18]=[C:19]([CH:20]=[C:1]([C:2](=[O:26])[CH3:3])[CH2:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH:22]=[CH:23][C:24]=1[F:25]

Participants

6

Reactant 3

HCID 962WaterHCID 5880883,4-DifluorobenzaldehydeHCID 12425357HCID 12425357, compound

Product 1

HCID 54072301HCID 54072301, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalyst

Procedure

A solution of benzyl propionylacetate (36.3 g, 176 mmol), 3,4-difluorobenzaldehyde (25.0 g, 176 mmol), piperidine (0.86 mL, 9.0 mmol) and acetic acid (0.49 mL, 9.0 mmol) was refluxed with removal of water using a Dean-Stark apparatus for 5 h. The solvent was removed in vacuo and the residue was dissolved in EtOAc. The reaction mixture was washed with water (100 mL), followed by brine (100 mL) and dried over anhydrous Na2SO4. The solvent was evaporated, giving a pale yellow syrup (60.2 g). The product was used in the next step without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe reaction mixture was washed with water (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ae753476871b49c499c00b7777dcc14f
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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