Réaction #809153

Équation de réaction

4,6-bis(trimethylsilyl)thianthrene-5-oxide

acetyl chloride

→

oil

Rendement 93.7%

1,9-Bis(trimethylsilyl)thianthrene

Rendement 93.7%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Autresolvent was removed in vacuo
2. 2
   Extractionthe residue was extracted with ether
3. 3
   LavageThe extract was washed with water and 1 M Na2S2O3 solution
4. 4
   Séchagedried with MgSO4
5. 5
   Autrethe solvent was removed in vacuo

Mode opératoire

To a stirred solution of 4,6-bis(trimethylsilyl)thianthrene-5-oxide (1.67 g, 4.44 mmole) and acetyl chloride (3.80 mL, 53.2 mmole) in acetone (75 mL), KI (17.00 g, 102.0 mmole) was added. After stirring at room temperature for 2 hrs, solvent was removed in vacuo and the residue was extracted with ether. The extract was washed with water and 1 M Na2S2O3 solution, dried with MgSO4, and the solvent was removed in vacuo to afford yellow oil (1.50 g, 86%). The product was eventually crystallized and used without further purification. mp 90˜91° C. (lit. 95˜96° C.). 1H NMR (300 MHz, CDCl3) δ: 7.47 (dd, 2H, J=7.5, 1.5 Hz), 7.42 (dd, 2H, J=7.5, 1.2 Hz), 7.20 (dd, 2H, J=7.5, 7.5 Hz), 0.46 (s, 18H). 13C NMR (125 MHz, CDCl3) δ: 142.4, 139.8, 134.3, 134.0, 129.6, 126.8, 0.52. HR-MS (ESI): calcd. for C18H24S2Si2+Na 383.0750 [(M+Na)+]. found 383.0747.

Source