Tetrahydrofuran → HCID 70131759, compound

Participants

Reaction Conditions

Reaction Steps

9.5 ml (1 mol) of vinyl magnesium bromide was gradually added to 50 ml of a dry tetrahydrofuran solution containing 1 g of 1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose under stirring at 0° C. under an inert atmosphere of nitrogen gas. 30 minutes later, the ice bath was removed, and stirring was further continued for 30 minutes at room temperature. Completion of the reaction was confirmed by thin layer chromatography, and then a small amount of water was added to inactivate any excess Grignard reagent. Then, the solvent was distilled off under reduced pressure. The obtained crude product was dissolved in 200 ml of ethyl acetate and washed three times with 200 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained syrup product was purified by silica gel column chromatography (ethyl acetate: hexane=1:2) to obtain 0.9 g of the desired product (Compound No. 27). The NMR analytical data of this product are as follows.

Provenance & Evidence