Phenylacetylene → BIS(PHENYLETHYNYL)DIMETHYLSILANE

HRID 1603291Notes

Reaction equation

HRID 1603291 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)#[CH:2].[CH2:9]([Li])[CH2:10][CH2:11][CH3:12].[CH3:14][SiH:15](Cl)[CH3:16]>C1COCC1>[C:3]1([C:1]#[C:2][Si:15]([C:9]#[C:10][C:11]2[CH:12]=[CH:4][CH:3]=[CH:1][CH:2]=2)([CH3:16])[CH3:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 66108ChlorodimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 11010735BIS(PHENYLETHYNYL)DIMETHYLSILANE

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 50 ml of tetrahydrofuran (TBF) solution containing 6 ml of ethynylbenzene, 33 ml of 1.6N normal-butyl lithium was added dropwise under a nitrogen gas flow at 0° C. After stirring for 1 hour, 33.3 ml of THF solution containing 3ml of dimethylsilyl chloride was added. After stirring at the room temperature for one night, the deposited solid was filtered and thereafter the obtained reaction solution was concentrated. Water was added to the solution, and then the solution was extracted with diethyl ether. Furthermore, the said diethyl ether layer was washed with water, thereafter dried with magnesium sulfate and concentrated. Then it was recrystallized from hexane, to obtain 5.02 g of bisphenylethynyldimethylsilane.

Workup

  1. additionwas added dropwise under a nitrogen gas flow at 0° C
  2. additionwas added
  3. stirringAfter stirring at the room temperature for one night
  4. filtrationthe deposited solid was filtered
  5. customthe obtained reaction solution
  6. concentrationwas concentrated
  7. additionWater was added to the solution
  8. extractionthe solution was extracted with diethyl ether
  9. washFurthermore, the said diethyl ether layer was washed with water
  10. dry with materialdried with magnesium sulfate
  11. concentrationconcentrated
  12. customThen it was recrystallized from hexane

Sources & evidence

ORD record
ord-057abca216db49788bbe6c8fcc4dd364
Source dataset
uspto-grants-1999_11
Patent number
US05986121

Reaction notes

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