preparation | 100ml eggplant bottle was sequentially added with (R)-3-butyne -2-alcohol (8.0g,0.114mol), THF(50ml), concentrated sulfuric acid (1 drop) and HMDS(29.6g,0.18mol), and the obtained white suspension was heated and refluxed for 4 hours. Add n-butyl lithium (2.5M,55ml,0.14mol) dropwise at -50 ~-40 ℃ to obtain light yellow clear liquid, and continue stirring for 1h. The mixed solution of THF(218ml) and toluene (87ml) of N,N-diphenyl-1H-imidazol-1-formamide (36g,0.136mol) was added dropwise to obtain orange clear liquid, quenched with 5N sulfuric acid (123ml,0.308mol), and stirred at 30 ℃ for 1h. In liquid separation, the organic phase is washed with 5N sulfuric acid (12.6ml,0.063mol) and saturated sodium chloride aqueous solution (32.0ml × 2), then the pH is adjusted with sodium bicarbonate solution to 7, and concentrated under reduced pressure to dry yellow solid Volapasa M-4 crude 32g. Toluene (30ml) was added to the crude product (10g,0.038mol) of Volapasa M-4, heated and refluxed for 2h, cooled to room temperature, filtered, vacuum dried to obtain 24.0g of yellow solid with a yield of 79.2%. |