2-(4-Fluorophenyl)-N-methoxy-N-methylacetamide → 1-(4-Fluorophenyl)but-3-en-2-one

HRID 1991354Notes

Reaction equation

HRID 1991354 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](N(OC)C)=[O:14])=[CH:8][CH:7]=1>C1COCC1.CCOCC.[Cl-].[Na+].O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](=[O:14])[CH:1]=[CH2:2])=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 210993112-(4-Fluorophenyl)-N-methoxy-N-methylacetamideHCID 178418507HCID 178418507, compound

Product 1

HCID 210992911-(4-Fluorophenyl)but-3-en-2-oneYield 81.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 220 mL (1.0 M, 220 mmol) of vinylmagnesium bromide in 100 mL THF, was added dropwise under nitrogen atmosphere at 0° C. a solution of 21 g (106.6 mmol) 2-(4-fluoro-phenyl)-N-methoxy-N-methylacetamide (step A) in ˜150 mL dry ether. The reaction mixture was stirred at 0° C. for 0.5 hr then poured slowly into an ice/2N aq HCl mixture. The resulting mixture was diluted with ether and brine, transferred to a separatory funnel and the organic layer separated. The organic layer was washed with brine, dried over drying agent, filtered and the solvent evaporated under vacuum to give 14.2 g of the crude title compound which was used without further purification. 1H-NMR (CDCl3): δ: 7.19 (2H, m), 7.02 (2H, t, J=9.5 Hz), 6.42 (1H, dd, J1=14.2 Hz, J2=11 Hz). 6.34 (1H, d, J=14.2 Hz), 5.86 (1H, d, J=11 Hz), 3.87 (2H, s).

Workup

  1. customtransferred to a separatory funnel
  2. customthe organic layer separated
  3. washThe organic layer was washed with brine
  4. customdried
  5. customover drying agent
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-055b77453d504b43b051f9058f5951b1
Source dataset
uspto-grants-2010_01
Patent number
US07645790B2

Reaction notes

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