Dichloromethane → HCID 58512387, compound

Temperature

0 °C

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%.

1. customto come to room temperature
2. waitthe stirring was continued for another 8 hours
3. customto terminate
4. customthe reaction
5. extractionthe aqueous layer was extracted with toluene
6. washThe combined organic layers were washed with water three times
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationThe solution was concentrated under reduced pressure
9. customthe residue was purified by column chromatography with toluene as an eluent

ORD record

ord-b77ec79fd05d40e592033233df3e4891

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580146B2