反应 #3713831
相关文献 (1)
openreactiondata ↗doi:10.6084/m9.figshare.5104873.v1; patent:US05484942
反应条件: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 9.38 g of 2-methoxyphenylacetic acid are added, at room temperature, to a suspension of 1.89 g of sodium hydride (80% dispersion in vaseline) in 200 cm3 of dry tetrahydrofuran. This suspension is cooled to -30° C., 7.77 cm3 of pivaloyl chloride are added and then a solution, cooled to -78° C., which is obtained by adding 35.27 cm3 of a 1.6M solution of butyllithium in hexane to a solution, cooled to -78° C., of 10 g of (4S,5S)-4-methyl-5-phenyl-2-oxazolidinone in 200 cm3 of dry tetrahydrofuran, is finally added. The reaction mixture is stirred for 45 minutes at -30° C. and then after reequilibrating to room temperature, 200 cm3 of a saturated aqueous solution of ammonium chloride is added followed by 500 cm3 of ethyl acetate; after decantation, the organic phase is washed twice with 100 cm3 of water and then twice with 100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 4.8 cm, height 36 cm), eluting under a nitrogen pressure of 0.6 bar with a cyclohexane and ethyl acetate mixture (85/15 and then 80/20 by volume) and collecting fractions of 50 cm3. Fractions 14 to 31 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). 13.6 g of (4S,5S)-4-methyl5-Phenyl-3-(2-methoxyphenylacetyl)-2-oxazolidinone are obtained in the form of a yellow oil. a solution, cooled to -78° C. which is obtained is finally added after reequilibrating to room temperature after decantation, the organic phase is washed twice with 100 cm3 of water twice with 100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulphate concentrated to dryness under reduced pressure (2.7 kPa) The residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 4.8 cm, height 36 cm) eluting under a nitrogen pressure of 0.6 bar with a cyclohexane and ethyl acetate mixture (85/15 80/20 by volume) and collecting fractions of 50 cm3 concentrated to dryness under reduced pressure (2.7 kPa)
来源 ID: ord-cbdf26f036934a3c93e0bac72f2166e8