反应详情

To an argon purged solution of methyl 3-(1-phenylvinyl)-5-(pyridin-2-yl)benzoate (73 mg, 0.23 mmol) in ethanol (5 mL) and HCl (conc. 1 mL) was added PtO2 (7 mg, 0.023 mmol). The mixture was hydrogenated under a hydrogen atmosphere (35 psi) for 6 h. The reaction mixture was purged with argon, filtered through a 0.2 μm filter, and concentrated. The resulting crude material was taken up with CH2Cl2 (5 mL) after which iPr2NEt (0.1 mL, 0.58 mmol) and acetyl chloride (18 μL, 0.25 mmol) were successively added. The mixture was stirred for 30 min, then diluted with CH2Cl2 (30 mL) and washed successively with 0.5 M HCl (1×10 mL), 9% sodium carbonate (1×10 mL), brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue containing the title compound was used without further purification. MS m/z=372 [M+1]+; Calc'd for C23H33NO3: 371.

1. customfor 6 h
2. customThe reaction mixture was purged with argon
3. filtrationfiltered through a 0.2 μm
4. filtrationfilter
5. concentrationconcentrated
6. additionwere successively added
7. washwashed successively with 0.5 M HCl (1×10 mL), 9% sodium carbonate (1×10 mL), brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. additionThe crude residue containing the title compound
12. customwas used without further purification