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

HRID 8544

Reaction equation

HRID 8544 reaction equation
[CH2:1]([Si:5]([CH3:22])([C:12]1([CH2:18][CH:19]([CH3:21])[CH3:20])SCCCS1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].[OH2:23]>CC#N.Cl[Hg]Cl>[CH2:1]([Si:5]([CH3:22])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:12](=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 2

HCID 962WaterHCID 22967180(3-Buten-1-yl)methyl[2-(2-methyl-1-propyl)-1,3-dithian-2-yl]phenylsilane

Product 1

HCID 222870621-[(3-Buten-1-yl)methylphenylsilyl]-3-methyl-1-butanone

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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 twice with 50-mL portions of hexane
  5. washThe combined organic extracts were washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-944f1193a82d4416b583f12b44d9cb7f
Source dataset
uspto-grants-2006_08
Patent number
US07087776B2

Linked notes

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