Tetrahydrofuran → HCID 57756003, compound

Temperature

70 °C

Tetrabutylammonium fluoride (1.0 M tetrahydrofuran solution, 420 μL, 0.416 mmol) was added to a tetrahydrofuran solution (500 μL) of (9S,12S,13S)-(E)-12,13-di-tert-butyldimethylsiloxy-9-hydroxy-10-octadecaenoic acid t-butyl ester (12) (11.6 mg, 0.189 mmol) at room temperature, and the mixture was stirred for 3 hours and 25 minutes. The temperature of the reaction solution was raised to 70° C., and the solution was stirred for 1 hour and 30 minutes. The temperature of the reaction solution was returned to room temperature, water (1 mL) was added, the mixture was extracted with chloroform (5 mL) three times, and the organic layer was washed with saturated brine (5 mL) dried over sodium sulfate, and concentrated. The resulting colorless oily crude product (20 mg) was separated and purified by silica gel column chromatography (toluene:ethyl acetate=1:2) to obtain (9S,12S,13S)-(E)-9,12,13-trihydroxy-10-octadecaenoic acid t-butyl ester (13) as a colorless oily substance (6.5 mg, 89%).

1. stirringthe solution was stirred for 1 hour and 30 minutes
2. customwas returned to room temperature
3. extractionthe mixture was extracted with chloroform (5 mL) three times
4. washthe organic layer was washed with saturated brine (5 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe resulting colorless oily crude product (20 mg) was separated
8. custompurified by silica gel column chromatography (toluene:ethyl acetate=1:2)

ORD record

ord-925dd4a30b134d53a6b5d869d9554098

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560484B2