Piperidine → Methyl 2-(4-fluorobenzylidene)-3-oxopentanoate

HRID 2293877Notes

Reaction equation

HRID 2293877 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[O:10]=[C:11]([CH2:17][CH3:18])[CH2:12][C:13]([O:15][CH3:16])=[O:14].N1CCCCC1>C1C=CC=CC=1.CCOCC.CC(O)=O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:12]([C:11](=[O:10])[CH2:17][CH3:18])[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 680234-FluorobenzaldehydeHCID 121699Methyl 3-oxovalerate

Product 1

HCID 53755005Methyl 2-(4-fluorobenzylidene)-3-oxopentanoateYield 70%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of para-fluorobenzaldehyde (37.98 gm, 306 mmol), 3-oxopentanoic acid, methyl ester (39.78 gm, 306 mmol), piperidine (2.60 gm, 30.6 mmol) and HOAc (0.555 gm, 9.2 mmol) was allowed to reflux in benzene (150 ml) 7 hours under argon. The solution was cooled to room temperature, then diluted with ether and washed with 2% HCl, saturated NaHCO3, water, and brine, then dried over MgSO4, filtered and concentrated to give a yellow oil. The oil was purified by distillation (bp=144° C. at 2.7 mm Hg) to give the title compound as a yellow oil (50.612 gm, 70%).

Workup

  1. washwashed with 2% HCl, saturated NaHCO3, water, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a yellow oil
  6. distillationThe oil was purified by distillation (bp=144° C. at 2.7 mm Hg)

Sources & evidence

ORD record
ord-c4b70c4875324c9d92e5be5a10c34bff
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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