Acetyl chloride → HCID 70132262, compound

Participants

Reaction Steps

2.4 ml (1.5 mol) of methyl lithium was gradually added to 30 ml of a dry tetrahydrofuran solution containing 0.3 g of 1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose under starting at 0° C. under an inert atmosphere of nitrogen gas. Completion of the reaction was confirmed by thin layer chromatography, and then 0.25 ml of acetyl chloride was added to the reaction mixture. The ice bath was removed, and the reaction solution was returned to room temperature and further stirred for one hour. The solvent was distilled off under reduced pressure. To the residue, 200 ml of ethyl acetate was added. The mixture was washed three times with 200 ml of a saturated sodium chloride aqueous solution. Then, the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (ethyl acetate: hexane=1:5) to obtain 0.29 g of the desired product (Compound No. 32). The NMR analytical data of this product are as follows.

Provenance & Evidence