Benzyl Alcohol → HCID 68247981, compound

Temperature

100 °C

3-Ethylcyclobutanecarboxylic acid (1.67 g) was dissolved in toluene (20 mL), and diisopropylethylamine (5.32 mL) was added thereto. The solution was heated to 100° C., and a solution of diphenylphosphoryl azide (3.09 mL) in toluene (10 mL) was added dropwise thereto over 40 minutes. After stirring at 100° C. for 15 minutes, benzyl alcohol (1.48 mL) was added, and the mixture was further stirred at 100° C. for 15 minutes. The reaction solution was cooled. A 0.2 N aqueous sodium hydroxide was added thereto, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=20/1-10/1) to obtain the title compound (1.81 g, diastereomeric mixture, trans:cis=1:1).

1. stirringthe mixture was further stirred at 100° C. for 15 minutes
2. temperatureThe reaction solution was cooled
3. extractionorganic matter was extracted with ethyl acetate
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. distillationthe solvent was distilled off under reduced pressure
7. customto obtain a crude product
8. customThis crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=20/1-10/1)

ORD record

ord-0f913c85956b4188b331866ba70c518d

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609710B2