تفاعل #8636

معادلة التفاعل

26

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

water

→

ketone

المردود 88.0%

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

المردود 88.0%

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 with hexane (50 mL)
5. 5
   غسيلThe combined organic extracts were washed with saturated aqueous NaCl
6. 6
   تجفيفdried over Na2SO4
7. 7
   تركيزConcentration to dryness in vacuo at rt

الإجراء التجريبي

To a solution of 26 (4.64 g 11.2 mmol) in CH3CN (300 mL) was added water (10 mL) and HgCl2 (15.26 g, 56.21 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 with hexane (50 mL). The combined organic extracts were washed with saturated aqueous NaCl and dried over Na2SO4. Concentration to dryness in vacuo at rt gave crude ketone 33 as a yellow oil (3.2 g, 88%): Rf=0.80 (1/9 EtOAc:hexane); 1H NMR (300 MHz, CDCl3) δ 7.58 (d, J=6.4 Hz, 4H), 7.44 (m, 6H), 5.88 (m, 1H), 4.99 (dd, J=17.1, 1.6 Hz, 1H), 4.91 (dd, J=10.2, 1.6 Hz, 1H), 2.50 (d, J=6.6 Hz, 2H), 2.14 (m, 2H), 1.36 (m, 2H), 0.95 (m, 1H), 0.76 (d, J=6.7 Hz, 6H); IR (neat) 3068 (m), 3046(m), 2956(s), 2925 (m), 2864 (m), 1956 (w), 1886 (w), 1826(w), 1641 (s), 1471 (m), 1431 (s), 1113 (s), 1000 (m), 910 (m), 743 (s), 702 (s) cm−1; MS (FAB) m/e (rel. intensity) 323 (MH+, 15), 322 (24), 321 (89), 267, (17), 236 (36), 198 (20), 182 (63), 169 (100), 167 (15), 159 (31); HRMS (FAB) calcd for C23H25OSi: 321.1675 (MH+-2), found: 321.1670.

المصدر