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0 °C

To a solution of diisopropylamine (6.3 mL, 45 mmol) in THF 100 mL at −78° C., was added n-butyllithilum (18 mL, 45 mmol of a 2.5M solution in hexanes). After 10 min. a solution (10 mL THF) of N-Allyl-4-trifluoromethoxy-benzamide 11 (5 g, 20 mmol) was added dropwise to the reaction mixture. The resulting dark blue reaction mixture was allowed to warm to 0° C. where it was quenched by addition of aqueous ammonium chloride. Ether was added and the organic layer was separated, dried (sodium sulfate), and concentrated. The residue was purified by silica gel chromatography (20% ether/hexanes) to provide the title compound (colorless solid 85%). 1H NMR (400 MHz, CDCl3) δ7.85 (d, J=8.8 Hz, 2 H, Ar), 7.55 (s, 1 H, NH), 7.29 (d, J=9.5 Hz, 2 H, Ar), 6.95 (m, 1 H, NHCHCH), 5.35 & 4.99 (m, 1 H, CHCHCH3), 1.72 (m, 3 H, CH3)

1. customThe resulting dark blue reaction mixture
2. customwas quenched by addition of aqueous ammonium chloride
3. additionEther was added
4. customthe organic layer was separated
5. dry with materialdried (sodium sulfate)
6. concentrationconcentrated
7. customThe residue was purified by silica gel chromatography (20% ether/hexanes)