Tetrahydrofuran → HCID 15240666, compound

HRID 1654621Notes

Reaction equation

HRID 1654621 reaction equation
O1CCCC1.[CH3:6][C:7]([N:16]([CH:27]([CH3:31])[C:28](=O)[CH3:29])[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)[CH3:8].C[O-].[Na+]>CO>[CH3:6][C:7]([N:16]1[CH:27]([CH3:31])[C:28]([CH3:29])=[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[C:17]1=[O:26])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)[CH3:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 15240665HCID 15240665, compound

Product 1

HCID 15240666HCID 15240666, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 20 ml of tetrahydrofuran were added 2.0 g of N-[1-methyl-1-(3-chlorophenyl)ethyl]-N-(1-methyl-2-oxopropyl)-2-(2-fluorophenyl)acetamide and 1.5 g of a 28% methanol solution of sodium methoxide, followed by stirring at room temperature for 5 minutes. After the solvent was distilled off, water was added, followed by extraction with ethyl acetate. After dried over anhydrous sodium sulfate, the solution was concentrated and then subjected to column chromatography to obtain 0.9 g of the desired 1-[1-methyl-1-(3-chlorophenyl)ethyl]-4,5-dimethyl-3-(2-fluorophenyl)-3-pyrroline-2-one.

Workup

  1. distillationAfter the solvent was distilled off
  2. additionwater was added
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialAfter dried over anhydrous sodium sulfate
  5. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-933de690de404e119345f923e714e184
Source dataset
uspto-grants-1995_04
Patent number
US05409886

Reaction notes

Loading…