Acetic Acid → HCID 367495, compound

HRID 1651525Notes

Reaction equation

HRID 1651525 reaction equation
N1CCCCC1.C(O)(=O)C.[C:11]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:12][C:13]([CH3:15])=[O:14].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.O>[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[C:12]([C:13](=[O:14])[CH3:15])[C:11]([O:17][CH2:18][CH3:19])=[O:16])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 367495HCID 367495, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Piperidine (4.0 mL) and glacial acetic acid (12 mL) were added to a stirred solution of ethyl acetoacetate (127.5 mL, 1.0 mol) and 4-fluorobenzaldehyde (136.52 g, 1.1 mol) in 200 mL of toluene. This mixture was heated under reflux for four hours with azeotropic removal of water. The reaction mixture was cooled to room temperature and concentrated. The residue was flash chromatographed on silica gel, eluting with toluene, to produce 226.0 g of crude product which was then distilled to yield 186.2 g of a mixture of cis- and trans-ethyl 2-[(4-fluorophenyl)methylene]-3-oxobutanoate, bp 160°-170° C. at 5 mm Hg.

Workup

  1. temperatureThis mixture was heated
  2. concentrationconcentrated
  3. customchromatographed on silica gel
  4. washeluting with toluene
  5. customto produce 226.0 g of crude product which
  6. distillationwas then distilled

Sources & evidence

ORD record
ord-ae86f881515940eab1fa8e751a4b685b
Source dataset
uspto-grants-1990_05
Patent number
US04929620

Reaction notes

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