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

Temperatur

0 °C

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-fluorophenyl)-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 (2 H, m), 7.02 (2 H, t, J=9.5 Hz), 6.42 (1 H, dd, J1=14.2 Hz, J2=11 Hz). 6.34 (1 H, d, J=14.2 Hz), 5.86 (1 H, d, J=11 Hz), 3.87 (2 H, s).

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

ORD-Eintrag

ord-9686f528df9e4bae9afe1b10dbefeddd

Quelldatensatz

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07345083B2