ethyl 2-fluoro-3-hydroxypropanoate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A crude product of 2-fluoro-3-hydroxypropionic acid ethyl ester (13.06 g) was dissolved in dichloromethane (300 ml). Imidazole (17.2 g, 252.57 mmol) and tert-butyldiphenylsilyl chloride (25 ml, 96.14 mmol) were added to the solution under cooling on ice, and the reaction solution was stirred for 18 hours while raising the reaction solution temperature to room temperature. Saturated sodium bicarbonate water was added to the reaction solution and the resultant was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 17.98 g (three steps, 57%) of the title compound in the form of a colorless clear oily product. under cooling on ice the resultant was extracted with dichloromethane The extract was dried over anhydrous sodium sulfate the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: An amount of thionyl chloride of 8.99 g (0.08 mol) was introduced at 20-25° C. into a dry 50 ml round-bottomed flask under a nitrogen atmosphere. Ethyl 3-hydroxy-2-fluoropropionate (10.0 g, 0.07 mol) were subsequently metered in in 1 h and the mixture was subsequently stirred at ambient temperature for a further 2 h. An amount of toluene of 3.98 g (0.04 mol), together with 0.286 g of pyridine (5 mol %), were introduced into a second round-bottomed flask with an Anschutz head and the mixture was heated to 80° C., The mixture from the 1st round-bottomed flask was added dropwise to the preheated solution in 1 h at 75-85° C. Solvents were distilled off under reduced pressure and the residue was subsequently finely distilled at 120° C. and 10 mbar. 4.1 g of distillate were obtained as a colorless liquid. were subsequently metered in in 1 h the mixture was heated to 80° C. The mixture from the 1st round-bottomed flask was added dropwise to the preheated solution in 1 h at 75-85° C Solvents were distilled off under reduced pressure the residue was subsequently finely distilled at 120° C. 4.1 g of distillate were obtained as a colorless liquid