Methyl iodide → 2-Methyl-2-(2-pyrrolidinylidene)-acetophenone

HRID 1413918Notes

Reaction equation

HRID 1413918 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[CH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[K].[CH3:16]C(C)([O-])C.CI.CC(C)([O-])C.[K+]>CN(C)C=O.C1C=CC=CC=1>[CH3:16][C:6](=[C:2]1[CH2:3][CH2:4][CH2:5][NH:1]1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 50987170Potassium tertbutoxideHCID 705738102-Pyrrolidinylidene-acetophenone

Product 1

HCID 705742772-Methyl-2-(2-pyrrolidinylidene)-acetophenone

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

17.0 g of α-(2-pyrrolidinylidene-acetophenone and 11.3 g of potassium-tert.-butoxide are dissolved in a mixture of 8 ml of dimethylformamide and 170 ml of benzene. A solution of 25 g of methyl iodide in 25 ml of benzene is added dropwise within 30 minutes. The reaction mixture heats up to 38°. It is stirred for 2 hours at room temperature; to the reaction mixture is then added a further 2.5 g of potassium tert.-butoxide and it is subsequently stirred for 15 hours at room temperature. The cloudy reaction mixture is filtered clear with the aid of diatomaceous earth; it is concentrated by evaporation and the evaporation residue is chromatographed on a silica-gel column with an ethyl acetate/hexane mixture (volume ratio 1:1). There is obtained 2-methyl-2-(2-pyrrolidinylidene)-acetophenone, m.p. 91°-92° (from cyclohexane).

Workup

  1. customheats up to 38°
  2. stirringis subsequently stirred for 15 hours at room temperature
  3. customThe cloudy reaction mixture
  4. filtrationis filtered clear with the aid of diatomaceous earth
  5. concentrationit is concentrated by evaporation
  6. customthe evaporation residue is chromatographed on a silica-gel column with an ethyl acetate/hexane mixture (volume ratio 1:1)

Sources & evidence

ORD record
ord-11396988253a4b00ba69adef9187c292
Source dataset
uspto-grants-1981_02
Patent number
US04251542

Reaction notes

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