Pyrrolidine → HCID 18987724, compound

HRID 1463280Notes

Reaction equation

HRID 1463280 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11](=[O:13])[CH3:12])[CH:5]=1.[CH3:16][C:17]([CH:19]([O:22][CH3:23])[O:20][CH3:21])=O.N1CCCC1>C1(C)C=CC=CC=1>[CH3:21][O:20][CH:19]([O:22][CH3:23])[C:17]1([CH3:16])[CH2:12][C:11](=[O:13])[C:6]2[CH:5]=[C:4]([O:3][C:2]([F:14])([F:15])[F:1])[CH:9]=[CH:8][C:7]=2[O:10]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 80650Pyruvic aldehyde dimethyl acetalHCID 27751021-[2-Hydroxy-5-(trifluoromethoxy)phenyl]ethan-1-one

Product 1

HCID 18987724HCID 18987724, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 0.5 g (2.27 mmole) of the compound obtained in step 2 dissolved in 10 ml of toluene were added 0.55 ml (4.54 mmole) of pyruvic aldehyde dimethyl acetal and 80 mg (1.14 mmole) of pyrrolidine. The reactants were heated to reflux for about 12 hours using Dean-Stark apparatus. After completion of the reaction, toluene solvent was removed therefrom under reduced pressure. The residue so obtained was extracted with ethyl acetate and concentrated to give residue, which was purified by silica gel column chromatography using as an eluent a mixture of hexane and ethyl acetate of 10:1 to obtain 0.470 g (yield 65%) of the title compound.

Workup

  1. temperatureThe reactants were heated
  2. temperatureto reflux for about 12 hours
  3. customwas removed
  4. customThe residue so obtained
  5. extractionwas extracted with ethyl acetate
  6. concentrationconcentrated
  7. customto give residue, which
  8. customwas purified by silica gel column chromatography
  9. additiona mixture of hexane and ethyl acetate of 10:1

Sources & evidence

ORD record
ord-541cf7aacaf445f28b503e8a1c6a2929
Source dataset
uspto-grants-1994_04
Patent number
US05300511

Reaction notes

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