p-Ethynyltoluene → Trimethyl({4-[(4-methylphenyl)ethynyl]phenyl}ethynyl)silane

Into a 50 ml round bottom flask was placed a mixture of 0.64 g (0.0054 mole) of 4-methylphenylacetylene, 1.50 g (0.005 mole) of 4-iodophenyltrimethylsilylacetylene, 0.011 g (0.0058 mmole) of CuI, 0.103 g (0.146 mmole) of bis(triphenylphosphine)palladium(II)dichloride in 10 ml of THF and 10 ml of triethylamine. The brown solution turned to an orange-yellow suspension when solid started to form. The mixture was stirred at room temperature under nitrogen for 3 days. It was filtered and the filtrate concentrated under reduced pressure. The residue was redissolved in 25 ml of chloroform and the solution was washed two times with water (15 ml each) and then dried over anhydrous MgSO4, filtered and concentrated, 1.43 g (quantitative yield) of solid was obtained. 1HNMR indicated ˜10% of by product present. The solid product was used for the next step without further purification.

1. customInto a 50 ml round bottom flask was placed
2. customto form
3. filtrationIt was filtered
4. concentrationthe filtrate concentrated under reduced pressure
5. dissolutionThe residue was redissolved in 25 ml of chloroform
6. washthe solution was washed two times with water (15 ml each)
7. dry with materialdried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORDレコード

ord-97abb2d95ea64fda9d9297cc58ff2adf

出典データセット

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08703388B2