Ammonium Chloride → HCID 10855562, compound

Participants

Reaction Conditions

Reaction Steps

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;

Provenance & Evidence