Ammonium Chloride → HCID 10855562, compound

Temperature

-20 °C

To dimethyl copper lithium solution prepared by adding 66.6 g of copper iodide (350 mmol) to 500 ml of methyl lithium (1.4 N, 700 mmol) according to a general method, 50 ml of anhydrous ether solution in which 44.1 g of levoglucosenone (350 mmol) is dissolved were added dropwise at -60° C. Thereafter, the resultant solution was stirred at -60° C. for thirty minutes, and then its reaction temperature was raised to -20° C. Next, the reacted solution was poured into saturated ammonium chloride aqueous solution, followed by stirring at room temperature for an hour, The resultant solution was filtered to remove insoluble substances. Next, the organic solvent layer was separated from the obtained filtrate. The residual aqueous layer was extracted with methylene chloride to obtain an extract, This extract and the organic layer as separated before were combined. The organic layer thus combined was washed with a saturated aqueous sodium chloride solution, and dried with anhydrous magnesium sulfate. The resultant organic layer was further filtered, and the filtrate was concentrated. The obtained residue was distilled under reduced pressure, thereby yielding 41.9 g of 1,6-anhydro-3,4-dideoxy-4-C-methyl-β-D-erythrohexopyranose-2-ulose (yield: 84.3%). This product exhibited the following physical properties;

1. dissolutionis dissolved
2. additionwere added dropwise at -60° C
3. customits reaction temperature
4. filtrationThe resultant solution was filtered
5. customto remove insoluble substances
6. customNext, the organic solvent layer was separated from the obtained filtrate
7. extractionThe residual aqueous layer was extracted with methylene chloride
8. customto obtain an extract
9. extractionThis extract
10. customthe organic layer as separated
11. washThe organic layer thus combined was washed with a saturated aqueous sodium chloride solution
12. dry with materialdried with anhydrous magnesium sulfate
13. concentrationthe filtrate was concentrated
14. distillationThe obtained residue was distilled under reduced pressure

ORD record

ord-780c2ecc41e94c6185ef0e557a57acd6

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05216177