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

HRID 8540

반응식

HRID 8540 반응식
[CH2:1]([Si:5]([C:18]1([CH2:24][CH:25]([CH3:27])[CH3:26])SCCCS1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].[OH2:28]>CC#N.Cl[Hg]Cl>[CH2:1]([Si:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:18](=[O:28])[CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:2][CH:3]=[CH2:4]

참가 물질

5

반응물 2

HCID 962WaterHCID 22287058(3-Buten-1-yl) [2-(2-methyl-1-propyl)-1,3-dithian-2-yl]diphenylsilane

생성물 1

HCID 153498501-[(3-Buten-1-yl)diphenylsilyl]-3-methyl-1-butanone수율 88%

시약·촉매·용매 2

HCID 24085Mercuric Chloride촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  1. concentrationthe mixture was concentrated
  2. custompartitioned between water (100 mL) and hexane (200 mL)
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer extracted with hexane (50 mL)
  5. washThe combined organic extracts were washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration to dryness in vacuo at rt

출처 및 근거

ORD 기록
ord-d41ccf720ab94cdf82e21c85e2c9b1d6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087776B2

연결된 노트

불러오는 중…