Dimethylformamide → 2-(4-Methoxy-2,3-dimethylphenyl)-1-(pyrrolidin-1-yl)ethanone

HRID 2423285Notes

Reaction equation

HRID 2423285 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH3:12])[C:5]=1[CH3:13].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.CN(C=[O:24])C>O.CCOCC>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C:2]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:24])=[C:5]([CH3:13])[C:6]=1[CH3:12]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 59864791HCID 59864791, compound

Product 1

HCID 598648482-(4-Methoxy-2,3-dimethylphenyl)-1-(pyrrolidin-1-yl)ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

Under an N2 atmosphere, 1-(2,2-dibromovinyl)-4-methoxy-2,3-dimethylbenzene was dissolved in a mixture of DMF (43 mL) and water (14 mL). Pyrrolidine (5.67 mL, 68 mmol) was added and the reaction was heated to 80° C. for 20 h. The reaction was diluted with Et2O and water. The layers were separated and the organic layer was washed with 0.25M HCl (aq) and brine. The organic extract was dried (Na2SO4), filtered, and concentrated in vacuo. Flash column chromatography of the residue, eluting with 0% to 100% ethyl acetate in hexanes, afforded the title compound. LC-MS ESI (pos.) m/z: 248.2 (M+H).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with 0.25M HCl (aq) and brine
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washFlash column chromatography of the residue, eluting with 0% to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ff444e80e37843a2800e226d1dabe5dd
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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