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ChemicalBook CAS DataBase List 2-(TRIMETHYLSILYL)NAPHTHALENE
18052-85-2

2-(TRIMETHYLSILYL)NAPHTHALENE synthesis

8synthesis methods
-

Yield: 76%

Reaction Conditions:

with potassium phosphate;chlorobis(ethylene)rhodium(I) dimer;C21H25N2(1+)*Cl(1-)*ClH;potassium tert-butylate;isopropyl alcohol in toluene at 180; for 16 h;Sealed tube;Inert atmosphere;Glovebox;

Steps:

IV. General Procedure for Rh-Catalyzed C-O Bond Reduction of Aryl Carbamates
General procedure: [RhCl(C2H4)2]2 (5.8 mg, 0.015 mmol), L2·HCl (21 mg, 0.060 mmol), KOtBu (7.4 mg, 0.066 mmol),K3PO4 (127 mg, 0.60 mmol), and toluene (0.40 mL) were added to a 5 mL screw-capped vial in aglovebox filled with nitrogen, and the resulting mixture was stirred at 60 °C for 1 h. Carbamate 1a(53 mg, 0.30 mmol), 2-propanol (18 mg, 0.30 mmol) and toluene (0.60 mL) were added to the vial inthe glove box. The vessel was stirred at 180 °C for 4 h followed by cooling to rt. The mixture waspurified by flash column chromatography over silica gel (eluting with hexane/EtOAc = 100/1) togive 2a as a white solid (36 mg, 78%).

References:

Yasui, Kosuke;Higashino, Masaya;Chatani, Naoto;Tobisu, Mamoru [Synlett,2017,vol. 28,# 19,p. 2569 - 2572] Location in patent:supporting information

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