Acetic Acid → HCID 54044562, compound

HRID 2295225Notes

Reaction equation

HRID 2295225 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:14])[CH:11]([CH3:13])[CH3:12].N1CCCCC1.CC(O)=O>C1C=CC=CC=1.O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:15]([C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 680234-FluorobenzaldehydeHCID 81583Ethyl isobutyrylacetate

Product 1

HCID 54044562HCID 54044562, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 4-fluorobenzaldehyde (3.00 gm, 24 mmol), ethyl isobutyrylacetate (3.82 gm, 24 mmol), piperdine (240 ul), and HOAc (42 ul) was refluxed in benzene (15 ml) with removal of water (Dean-Stark trap) for 22 hours. The cooled mixture was diluted with Et20 and washed successively with 2% HCl, saturated NaHCO3, H2O, and brine, then dried (Na2SO4), filtered, and stripped to yield an oil. Distillation of the oil (bp 110°-113° C. at 0.25 mm) afforded the title compound (5.32 gm, 83%) as a pale yellow liquid. This reaction has been successfully scaled up to 300 mmol.

Workup

  1. additionThe cooled mixture was diluted with Et20
  2. washwashed successively with 2% HCl, saturated NaHCO3, H2O, and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customto yield an oil
  6. distillationDistillation of the oil (bp 110°-113° C. at 0.25 mm)

Sources & evidence

ORD record
ord-d3b79f2d003d4013b3ec469cfcb6076e
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

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