Water → Triisopropyl-(4-selenophen-2-ylphenoxy)silane

HRID 1873424Notes

Reaction equation

HRID 1873424 reaction equation
[Se:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH:20]([Si:23]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])Cl)([CH3:22])[CH3:21].O>CN(C1C=CN=CC=1)C.ClCCl>[CH:20]([Si:23]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[O:12][C:9]1[CH:10]=[CH:11][C:6]([C:2]2[Se:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][CH:8]=1)([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 139400Triisopropylsilyl chlorideHCID 126128064-Selenophen-2-ylphenol

Product 1

HCID 86644790Triisopropyl-(4-selenophen-2-ylphenoxy)silane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

8.0 g (35.9 mmol) of 4-selenophen-2-ylphenol are initially introduced together with 50 ml (0.36 mol) of triethylamine and 0.44 g (3.6 mmol) of DMAP in 100 ml of dichloromethane, and 20 ml (93.5 mmol) of triisopropylchlorosilane are added. When the addition is complete, the mixture is warmed under reflux for 3 h. After cooling, the reaction mixture is added to water, and the organic phase is separated off. The aqueous phase is extracted with dichloromethane, and the combined organic phase is washed with sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1). Further purification is carried out by further column chromatography (SiO2, n-heptane:toluene=4:1); triisopropyl-(4-selenophen-2-ylphenoxy)silane is obtained as a yellow oil.

Workup

  1. additionare added
  2. additionWhen the addition
  3. temperaturethe mixture is warmed
  4. temperatureunder reflux for 3 h
  5. temperatureAfter cooling
  6. customthe organic phase is separated off
  7. extractionThe aqueous phase is extracted with dichloromethane
  8. washthe combined organic phase is washed with sat. sodium chloride soln
  9. customThe solution is dried
  10. concentrationconcentrated to dryness
  11. customThe residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1)
  12. customFurther purification

Sources & evidence

ORD record
ord-e6b15c910c6c4260af8180d2601bf405
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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