1-Phenyl-2-butanone → 1-(Dimethylamino)-2-phenylpent-1-en-3-one

HRID 1471894Notes

Reaction equation

HRID 1471894 reaction equation
[C:1]1([CH2:7][C:8](=[O:11])[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>CN(C=O)C>[CH3:14][N:15]([CH3:17])[CH:16]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8](=[O:11])[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 138791-Phenyl-2-butanoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 673843211-(Dimethylamino)-2-phenylpent-1-en-3-oneYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-phenylbutan-2-one (5.00 g, 33.7 mmol) in DMF (80.0 mL) was added 1,1-dimethoxy-N,N-dimethylmethanamine (6.03 g, 50.6 mmol). The resulting mixture was stirred at 90° C. for 16 h. Upon completion, the reaction mixture was quenched with water (40.0 mL), extracted with EtOAc (4×50.0 mL), and washed with brine. The combined organics were dried over MgSO4, filtered, and concentrated to give a brown oil. This brown oil was purified by flash chromatography to give the title compound as a yellow oil (3.32 g). 1H NMR (400 MHz, CDCl3) δ ppm 0.97 (t, J=7.32 Hz, 3H), 2.19 (q, J=7.49 Hz, 2H), 2.67 (s, 6H), 7.14-7.41 (m, 5H), 7.61 (s, 1H).

Workup

  1. customUpon completion, the reaction mixture was quenched with water (40.0 mL)
  2. extractionextracted with EtOAc (4×50.0 mL)
  3. washwashed with brine
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customThis brown oil was purified by flash chromatography

Sources & evidence

ORD record
ord-d88544133f3845f19ab50be2f872cf04
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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