تفاعل #8640

معادلة التفاعل

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

المذيبات

CH3CN

ظروف التفاعل

المعالجة

1. 1
   تركيزthe mixture was concentrated
2. 2
   أخرىpartitioned between water (100 mL) and hexane (200 mL)
3. 3
   أخرىThe organic layer was isolated
4. 4
   استخلاصthe aqueous layer extracted twice with 50-mL portions of hexane
5. 5
   غسيلThe combined organic extracts were washed with saturated aqueous NaCl
6. 6
   تجفيفdried over Na2SO4

الإجراء التجريبي

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).

المصدر