Diethyl Malonate → HCID 19014385, compound

HRID 1728664Notes

Reaction equation

HRID 1728664 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]([CH:7]=[CH:8][C:9]([N-:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:10])=[CH:5][CH:4]=1.[C:21]([O:29][CH2:30][CH3:31])(=[O:28])[CH2:22][C:23]([O:25]CC)=O.[O-]CC.[Na+]>COCCOCCOC>[F:1][C:2]([F:19])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([CH:7]2[CH2:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:23](=[O:25])[CH:22]2[C:21]([O:29][CH2:30][CH3:31])=[O:28])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 178446544HCID 178446544, compound

Product 1

HCID 19014385HCID 19014385, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

105 mmol 4-trifluoromethylcinnamoyl-N-pentylamide, 116 mmol diethyl malonate, and 285 mmol sodium ethoxide were refluxed in a 1:1 touene/diglyme mixture for 7 h, cooled and washed with dilute HCl and water. Evaporation at 2 torr gave a dark red oil, which was purified by column chromatography on silica to give 23 g 4-(4-trifluoromethyl-phenyl)-3-ethoxycarbonyl-1-pentylpiperidine-2,6-dione as a reddish oil. 57 mmol 4-(4-trifluoromethylphenyl)-3-ethoxycarbonyl-1-pentylpiperidine-2,6-dione in 100 ml THF was slowly added with stirring to a suspension of 260 mmol LiAlH4 in 100 ml THF maintaining the temperature at 10° C., followed by stirring at room temperature overnight. Excess hydride was destroyed by addition of water, followed by 500 ml 4 N HCl. The THF was removed by evaporation, the aqueous phase was extracted by methylene chloride, and the organic phase was washed with 4 N NaOH, dried, and evaporated. Column chromatography on silica yielded the pure compound, which was crystallized from EtOAc. Compound (93). Yield 3.7 g. M.p. 112°-115° C.

Workup

  1. temperaturecooled
  2. washwashed with dilute HCl and water
  3. customEvaporation at 2 torr
  4. customgave a dark red oil, which
  5. customwas purified by column chromatography on silica

Sources & evidence

ORD record
ord-49b801958a1b475883d65529951e65b6
Source dataset
uspto-grants-1994_07
Patent number
US05328917

Reaction notes

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