Water → HCID 131723470, compound

HRID 2306514Notes

Reaction equation

HRID 2306514 reaction equation
C([Si:5](C)([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)CC=C.[OH2:23]>CC#N.Cl[Hg]Cl>[CH2:11]([CH2:10][C:6]1([SiH2:5][C:12](=[O:23])[CH2:18][CH:19]([CH3:20])[CH3:21])[CH:7]=[CH:8][CH:9]=[CH:10][CH2:11]1)[CH2:6][CH:7]=[CH2:8]

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 131723470HCID 131723470, compound

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 44 (6.19 g, 17.7 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-c500b139405244ce899246fccd4c01f4
Source dataset
uspto-grants-2002_08
Patent number
US06441212B1

Reaction notes

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