反応 #6632

反応方程式

4,4,7-trimethyl-6-bromothiochroman

Compound 66

4,4,7-trimethyl-6-bromothiochroman

trimethylsilyl acetylene

→

title compound

4,4,7-Trimethyl-6-trimethylsilylethynyl-thiochroman

溶媒

triethylamine

反応条件

後処理

1. 1
   その他was degassed under nitrogen
2. 2
   温度The mixture was then heated under a nitrogen atmosphere in the sealed tube at 100 degrees C
3. 3
   workup.WAITfor a further 64 h
4. 4
   その他The triethylamine was then removed under vacuum
5. 5
   その他the residue purified by flash chromatography (silica; hexanes)

実験手順

A mixture of 624 mg (3.0 mmol) of 4,4,7-trimethyl-6-bromothiochroman (Compound 66) 314 mg (3.2 mmol) of trimethylsilyl acetylene, 40 mg (0.21 mmol) of cuprous iodide, 80 mg (0.11 mmol) of bis (triphenylphosphin) palladium (II) chloride and 1 ml of triethylamine was degassed under nitrogen and heated in a sealed tube at 85 degrees C. for 15 h. The mixture was then treated with a further 20 mg (0.11 mmol) of cuprous iodide and 40 mg (0.06 mmol) of the palladium (II) catalyst. The mixture was then heated under a nitrogen atmosphere in the sealed tube at 100 degrees C. for a further 64 h. The triethylamine was then removed under vacuum and the residue purified by flash chromatography (silica; hexanes) to give the title compound as a yellow oil. PMR (CDCl3) δ 0.28 (9H, s), 1.30 (6H, s), 1.88-1.97 (2H, m), 2.33 (3H, s), 2.97-3.05 (2H, m), 6.92 (1H, s), 7.43 (1H, s).

出典