Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(4-Fluoro-2-propylamino-phenyl)-acrylic acid methyl ester

Temperature

-35 °C

To a solution of N-methoxy-N-methyl-4-fluoro-2-propylamino-benzamide (0.33 g, 1.37 mmol) in THF (4 mL) was added dropwise LiAlH4 (1 M in THF, 0.7 mL) at −45° C. The mixture was stirred for 40 minutes at −35° C. and then quenched by adding saturated aqueous KHSO4 solution. The mixture was diluted with EtOAc, washed with 3 N HCl, and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was reacted with methyl (triphenylphosphoranylidene)acetate (0.5 g, 1.5 mmol) in toluene (4 mL) overnight at 100° C. The mixture was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound (0.23 g, 69%) after purification by column chromatography (EtOAc:hexane=1:10).

1. customquenched
2. additionby adding saturated aqueous KHSO4 solution
3. additionThe mixture was diluted with EtOAc
4. washwashed with 3 N HCl, and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. washThe mixture was washed with water
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD record

ord-354b6e60db4b4814b8e31d0feb235318

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557872B2