Sulfuric Acid → HCID 70132997, compound

Temperature

-20 °C

100 mg of 1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose was dissolved in 3 ml of propionic anhydride, and the solution was cooled to -20° C. Then, 0.06 ml of concentrated sulfuric acid was added thereto, and the mixture was stirred for 30 minutes. Then, the reaction mixture was added to 100 ml of an ice-cooled saturated sodium hydrogencarbonate aqueous solution. The mixture was stirred for 30 minutes and then extracted with 100 ml of ethyl acetate. The extract was washed three times with 100 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained syrup crude product was purified by silica gel column chromatography (ethyl acetate: hexane=1:2) to obtain 100 mg of the desired product (Intermediate No. 19) as a colorless transparent liquid. The NMR analytical data of this product are as follows.

1. stirringThe mixture was stirred for 30 minutes
2. extractionextracted with 100 ml of ethyl acetate
3. washThe extract was washed three times with 100 ml of a saturated sodium chloride aqueous solution
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. customThe obtained syrup crude product was purified by silica gel column chromatography (ethyl acetate: hexane=1:2)

ORD record

ord-e74dff0907544a54a660a24883164667

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05380834