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ChemicalBook CAS DataBase List (Z)-2-Butenoic acid ethyl ester
6776-19-8

(Z)-2-Butenoic acid ethyl ester synthesis

10synthesis methods
-

Yield: 86 % ee

Reaction Conditions:

with hydrogen in ethanol at 100; under 15001.5 Torr; for 2 h;Autoclave;Sealed tube;stereoselective reaction;

Steps:

2.4 Semi-hydrogenation of alkynes
General procedure: Catalytic tests of Ni3N/NC or Ni/NC were performed as follows: 1,2-diphenylethyne (5.38mmol), Ni/NC or Ni3N/NC catalyst (7.8mol%, based on ICP results) and solvent (70mL) were mixed in a stainless-steel autoclave (100mL) equipped with an electric heating system and a magnetically driven mechanical stirrer. The reaction system was flushed with hydrogen three times and pressurized with hydrogen (2.0MPa), and then heated to 100°C for hydrogenation. After the completion of reaction, it was allowed to cool to room temperature and the residual hydrogen was released. The solvent was removed under reduced pressure, and the crude products were purified by column chromatography on silica gel to withhold the catalyst. For the substrate scope, the semi-hydrogenation of alkynes was conducted using a similar method. For a typical run: the alkyne (0.3mmol), 7.8mol% Ni3N/NC-6/5-550 and ethanol (3mL) were placed in a glass vial (4mL) with cap, septum, and needle, and then two glass vials were sealed in a stainless steel autoclave (100mL) equipped with an electrical heating system, where a certain amount of ethanol was added to keep the same horizontal level of ethanol inside and outside the glass vials. Then, the reaction system was treated following the same steps as described above.

References:

Shi, Xiaozhen;Wen, Xin;Nie, Shilin;Dong, Jie;Li, Jingde;Shi, Yongqing;Zhang, Huiling;Bai, Guoyi [Journal of Catalysis,2020,vol. 382,p. 22 - 30]