trimethylsilyl cyanate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,4-dimethoxybenzaldehyde (2.00 g, 12.04 mM) and trimethylsilyl cyanate (1.57 g, 15.04 mM) were dissolved in dry methylene chloride (1 ml). While stirring at room temperature, zinc iodide (8.5 mg) was carefully added and the mixture was stirred for 2 hours. Next, the solution was dropwise added to a solution of lithium aluminum hydride (1.10 g, 28.88 mM) in dried tetrahydrofuran (120 ml) cooled to 0° C., then the reaction temperature was gradually warmed to room temperature and the mixture was stirred for 1 hour. Water (2 ml) was carefully added while cooling the reaction solution in an ice bath, the mixture was stirred for 1 hour, then the solution was filtered through Celite. The filtrate was dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo to obtain a crude product (2.37 g) as a yellow solid. The crude product thus obtained had a sufficient purity even without purification, so could be used for the next reaction as it was. the mixture was stirred for 2 hours cooled to 0° C. the reaction temperature was gradually warmed to room temperature the mixture was stirred for 1 hour while cooling the reaction solution in an ice bath the mixture was stirred for 1 hour the solution was filtered through Celite The filtrate was dried over anhydrous magnesium sulfate the solvent was evaporated in vacuo to obtain a crude product (2.37 g) as a yellow solid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 4-(trifluoromethyl)benzaldehyde (500 μL, 3.66 mmol) and trimethylsilyl cyanate (537 μL, 4.03 mmol), lithium chloride (a 0.307 mol/L solution in tetrahydrofuran, 1.2 μL, 0.366 μmol) was added and the mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. The reaction mixture was diluted with diethyl ether (10 mL). To this, a 10% solution of hydrogen chloride in methanol (10 mL) was added at 0° C. and the mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated, water was added thereto, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give methyl hydroxy-4-(trifluoromethyl)phenylacetate (Compound CH) (587 mg, yield: 68%). was added the mixture was stirred at room temperature for 24 hours The reaction mixture was concentrated water was added extraction with ethyl acetate by washing with brine drying over anhydrous sodium sulfate The solvent was evaporated off under reduced pressure the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)