Reaction #2286332

Reaction equation

4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenol

4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenol

1,4-diazabicyclo[2.2.2]octane

dimethylthiocarbamoyl chloride

→

dimethyl-thiocarbamic acid O-{4-[2-(tert-butyl-diphenyl-silanyloxy)ethyl]-2,6-dichloro-phenyl}ester

Yield 90.5%

Solvents

N,N-dimethylformamide

ethyl acetate

Conditions

Workup

1. 1
   Washwas then washed with a 1N aqueous hydrochloric acid solution, water
2. 2
   Dryinga saturated aqueous sodium chloride solution, dried with magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated under vacuum

Procedure

A solution of 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenol (70) (289 mg, 0.78 mmol) in N,N-dimethylformamide (4 mL) at 25° C. was treated with 1,4-diazabicyclo[2.2.2]octane (172 μL, 1.56 mol) and dimethylthiocarbamoyl chloride (154 mg, 1.25 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was diluted with ethyl acetate and was then washed with a 1N aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution, dried with magnesium sulfate, filtered and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 95:5 petroleum ether/ethyl acetate) afforded dimethyl-thiocarbamic acid O-{4-[2-(tert-butyl-diphenyl-silanyloxy)ethyl]-2,6-dichloro-phenyl}ester (71) (376 mg, 90%) as a white solid; EI(+)-HRMS m/e calcd for C27H31Cl2N2O2SSi (M+H)+ 532.1295, found 532.1292. Exact Mass=531.1222; Molecular weight=532.61

Source