Réaction #44009

Équation de réaction

69

(E)-4-chloro-N-(pyrimidin-5-ylmethylene)benzenesulfonamide

2-(trimethylsilyl)-1,3-butadiene

THF

→

71

Rendement 40.0%

1-(4-chlorophenylsulfonyl)-2-(pyrimidin-5-yl)piperidin-4-one

Rendement 40.0%

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was heated
2. 2
   Températureat reflux for 36 hours
3. 3
   Concentrationconcentrated in vacuo
4. 4
   Autreto yield 3.33 g crude material
5. 5
   AutreThe residue was purified by flash chromatography (3:1 hexanes/EtOAc)

Mode opératoire

To a solution of 69 (2.12 g, 7.5 mmol) in THF (15 mL) was added 2-(trimethylsilyl)-1,3-butadiene (70, 2.18 g, 15 mmol). The reaction was heated at reflux for 36 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo to yield 3.33 g crude material. The residue was purified by flash chromatography (3:1 hexanes/EtOAc) to yield 1.05 g (40%) 71 as a yellow solid. 1H NMR (CDCl3) δ 9.16 (s, 1H), 8.63 (s, 2H), 7.85 (d, 2H), 7.55 (d, 2H), 5.65 (d, 1H), 4.11-4.04 (m, 1H), 3.24-3.14 (m, 1H), 2.96-2.82 (m, 2H), 2.55-2.49 (m, 1H), 2.40-2.34 (m, 1H).

Source