反応 #8640

反応方程式

44

(3-Buten-1-yl)methyl[2-(2-methyl-1-propyl)-1,3-dithian-2-yl]phenylsilane

water

→

ketone

1-[(3-Buten-1-yl)methylphenylsilyl]-3-methyl-1-butanone

溶媒

CH3CN

反応条件

後処理

1. 1
   濃縮the mixture was concentrated
2. 2
   その他partitioned between water (100 mL) and hexane (200 mL)
3. 3
   その他The organic layer was isolated
4. 4
   抽出the aqueous layer extracted twice with 50-mL portions of hexane
5. 5
   洗浄The combined organic extracts were washed with saturated aqueous NaCl
6. 6
   乾燥dried over Na2SO4

実験手順

To a solution of 44 (6.19 g, 177 mmol) in CH3CN (200 mL) was added water (10 mL) and HgCl2 (24 g, 88 mmol). After stirring overnight at rt, the mixture was concentrated and partitioned between water (100 mL) and hexane (200 mL). The organic layer was isolated and the aqueous layer extracted twice with 50-mL portions of hexane. The combined organic extracts were washed with saturated aqueous NaCl and dried over Na2SO4. Concennation to dryness in vacuo at rt gave quantitatively crude ketone 45 as a yellow oil. This ketone was used in the next reaction without further purification: Rf=0.75 (1/19 EtOAc:hexane); 1H NMR (300 MHz, CDCl3) δ 7.54–7.51 (m, 2H), 7.41–7.35 (m, 3H), 5.91–5.78 (m, 1H), 4.99 (dd, J=17.0, 1.7 Hz, 1H), 4.90 (dd, J=10.0, 1.7 Hz, 1H), 2.44 (d, J=6.7 Hz, 2H), 2.16–2.06 (m, 3H), 1.16–1.07 (m, 2H), 0.78 (pd. J=6.7 Hz, 6H), 0.51 (s, 3H).

出典