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

HRID 8540

Reaktionsgleichung

Reaktionsgleichung von HRID 8540
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24085Mercuric ChlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d41ccf720ab94cdf82e21c85e2c9b1d6
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087776B2

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