Ethyl Acetate → HCID 118109067, compound

440 mg of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H)-one (Dess-Martin Periodinane) was added to a solution of 200 mg of 1-benzyloxy-5-hydroxypentan-2-yl methanesulfonate in 2 mL of dichloromethane, and the obtained mixture was then stirred at room temperature for 1 hour. Thereafter, 100 mg of Dess-Martin Periodinane was added to the reaction mixture, and the thus obtained mixture was then stirred at room temperature for 1 hour. Thereafter, the reaction mixture was added to a mixture of 50 mL of ethyl acetate and 30 mL of a saturated sodium hydrogen carbonate aqueous solution, and the obtained mixture was then filtrated with Celite. The organic layer was fractionated. The obtained organic layer was washed with 30 mL of a sodium thiosulfate aqueous solution twice, and then with 30 mL of a saturated sodium chloride aqueous solution, and it was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (ethyl acetate/hexane=1/2 to 1/1), so as to obtain 141 mg of 1-benzyloxy-5-oxopentan-2-yl methanesulfonate in the form of a colorless oily product.

1. stirringthe thus obtained mixture was then stirred at room temperature for 1 hour
2. filtrationthe obtained mixture was then filtrated with Celite
3. washThe obtained organic layer was washed with 30 mL of a sodium thiosulfate aqueous solution twice
4. dry with materialwith 30 mL of a saturated sodium chloride aqueous solution, and it was then dried over anhydrous sodium sulfate
5. distillationThe solvent was distilled away under reduced pressure
6. customthe obtained residue was then purified by silica gel column chromatography (ethyl acetate/hexane=1/2 to 1/1)

ORD record

ord-5ce425d09ce947af9012f5b710043f74

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221865B2