Brief introduction of 344-14-9

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General procedure: A test tube chargedwith MS 3A (40.0 mg, 200 mg/mmol) was flame-dried under reduced pressure using a heat gun. After cooling to room temperature, argon was re-filled, Schiff base 1 (11.1 mg, 0.02 mmol), THF (0.2 mL) andGd(OiPr)3 (0.2 M THF solution, 0.1 mL, 0.02 mmol) were added. The mixture was stirred at roomtemperature for 30 min to afford yellow suspension. THF was, then, removed under reduced pressure. Tothe test tube were added Y(OTf)3 (10.7 mg, 0.02 mmol) and THF (0.20 mL), and the mixture was stirred at room temperature for 30 min to afford the Gd(OiPr)3/Y(OTf)3/Schiff base = 1:1:1 catalyst in THF.Then, DMAP (2.4 mg, 0.02 mmol) was added, and THF was removed under reduced pressure. After drying the residue under reduced pressure for 1 h at room temperature, toluene (0.2 mL) and Et2O (0.4mL) were added. To the resulting red suspension were added 2-fluoromalonate 3 (0.35 mmol, 1.7 equiv)and meso-aziridine 2 (0.20 mmol, 1.0 equiv), and the mixture was stirred for 17-72 h at 40 C. After themixture was cooled to room temperature and diluted with AcOEt, saturated EDTA?2Na aq. was added.The organic layer was separated, and the aqueous layer was extracted with AcOEt and the organic layers were washed with brine. The organic layers were dried over Na2SO4. After filtration and evaporation, the obtained crude mixture was purified by silica gel column chromatography (AcOEt/hexane/CH2Cl2) togive a corresponding product.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fukagawa, Seiya; Xu, Yingjie; Anada, Masahiro; Yoshino, Tatsuhiko; Matsunaga, Shigeki; Heterocycles; vol. 94; 7; (2017); p. 1337 – 1350;,
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