반응 #44009

반응 방정식

69

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

2-(trimethylsilyl)-1,3-butadiene

THF

→

71

수율 40.0%

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

수율 40.0%

반응 조건

후처리

1. 1
   온도The reaction was heated
2. 2
   온도at reflux for 36 hours
3. 3
   농축concentrated in vacuo
4. 4
   기타to yield 3.33 g crude material
5. 5
   기타The residue was purified by flash chromatography (3:1 hexanes/EtOAc)

실험 절차

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).

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