Dichloromethane → HCID 58512387, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-hydroxycyclohexylcarboxylate (s36) (26.0 g), 2,6-lutidine (23.3 g) and methylene chloride (200 ml) were placed in a reaction vessel under an atmosphere of nitrogen, and cooled to 0° C. Triisopropylsilyl trifluoromethanesulfonate (50 g) was added dropwise in the temperature range of 0° C. to 5° C. After 1 hour of stirring at 0° C., the reaction mixture was allowed to come to room temperature, and the stirring was continued for another 8 hours. Methanol was added to the reaction mixture to terminate the reaction. The reaction mixture was treated with water, and the aqueous layer was extracted with toluene. The combined organic layers were washed with water three times, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by column chromatography with toluene as an eluent and silica gel as a stationary phase powder to give ethyl 4-triisopropylsilyloxycyclohexylcarboxylate (37) (43.4 g). The yield based on the compound (s36) was 87.5%.

Provenance & Evidence