HCID 19025021, compound → HCID 19025015, compound

HRID 1033936Notes

Reaction equation

HRID 1033936 reaction equation
[CH3:1][C:2]1[CH2:6][N:5]([C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=O)[C:4](=[O:13])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:20]([Li])[CH2:21][CH2:22][CH3:23]>O1CCCC1.CCCCCC>[CH3:11][C:7]([N:5]1[CH2:6][C:2]([CH3:1])=[C:3]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:4]1=[O:13])([CH3:12])[C:8](=[O:10])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 19025021HCID 19025021, compoundHCID 178418339Butyllithium

Product 1

HCID 19025015HCID 19025015, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

5 g (19.3 mmol) of 2-(4-methyl-2-oxo-3-phenyl-3-pyrrolin-1-yl)isobutyric acid was dissolved in 50 ml of tetrahydrofuran, and a solution of 41 g (97 mmol) of 15% n-butyl lithium in n-hexane was dropwise added at 0° C. under a nitrogen stream. After completion of the dropwise addition, the mixture was stirred at room temperature for one day. The reaction solution was poured into ice water and extracted with ethyl acetate. The extract was treated by a conventional method, and the crude product thereby obtained was purified by column chromatography to obtain 2.7 g (yield: 47%) of the desired product having a melting point of from 87° to 89° C.

Workup

  1. additionAfter completion of the dropwise addition
  2. extractionextracted with ethyl acetate
  3. additionThe extract was treated by a conventional method
  4. customthe crude product thereby obtained
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f7a758be565a4bb08e2dca731af0c9bc
Source dataset
uspto-grants-1994_05
Patent number
US05312929

Reaction notes

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