3-乙基-2-硫代-4-恶唑烷酮

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A toluene (10 mL) solution of 3-ethyl-2-thioxooxazolidin-4-one 3 (145 mg, 1.0 mmol) and Lawesson's reagent (607 mg, 1.5 mmol) was refluxed overnight. The solution was cooled and diluted with ethyl acetate (100 mL), then washed with water (2×20 mL). The organic layer was dried with brine and MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=10:1), and the desired product 6 was obtained in 94% yield (152 mg, orange oil). 1H NMR (400 MHz, CDCl3): δ 5.12 (s, 2H), 4.21 (q, J=7.2 Hz, 2H), 1.29 (t, J=7.2 Hz, 3H). The solution was cooled washed with water (2×20 mL) The organic layer was dried with brine and MgSO4 concentrated in vacuo The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=10:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A toluene (10 mL) solution of 3-ethyl-2-thioxooxazolidin-4-one 3 (145 mg, 1.0 mmol) and Lawesson's reagent (607 mg, 1.5 mmol) was refluxed overnight. The solution was cooled and diluted with ethyl acetate (100 mL), then washed with water (2×20 mL). The organic layer was dried with brine and MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=10:1), and the desired product 6 was obtained in 94% yield (152 mg, orange oil). 1H NMR (400 MHz, CDCl3): δ 5.12 (s, 2H), 4.21 (q, J=7.2 Hz, 2H), 1.29 (t, J=7.2 Hz, 3H). The solution was cooled washed with water (2×20 mL) The organic layer was dried with brine and MgSO4 concentrated in vacuo The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=10:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of 3-ethyl-2-thioxooxazolidin-4-one 3 (145 mg, 1.0 mmol), 5-phenyl-2-furaldehyde 4 (172 mg, 1.0 mmol) and sodium acetate (410 mg, 5.0 mmol) was added acetic acid (5 mL). The reaction mixture was refluxed for 30 h, then the excess solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), then washed with water (2×20 mL). The organic layer was dried with brine and MgSO4, then concentrated in vacuo. The desired product 5 (JL101) was obtained by recrystallization from an ethyl acetate/hexanes mixture in 45% yield (135 mg, light yellow needles). 1H NMR (400 MHz, CDCl3): 7.81-7.76 (m, 2H), 7.44 (dt, J=8.0, 1.6 Hz), 7.36 (t, J=6.0 Hz, 1H), 7.28 (d, J=3.6 Hz, 1H), 6.88 (d, J=3.6 Hz, 1H), 6.80 (s, 1H), 3.97 (q, J=7.2 Hz, 2H), 1.34 (t, J=7.2 Hz, 3H). The reaction mixture was refluxed for 30 h the excess solvent was removed in vacuo The residue was diluted with ethyl acetate (100 mL) washed with water (2×20 mL) The organic layer was dried with brine and MgSO4 concentrated in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of 3-ethyl-2-thioxooxazolidin-4-one 3 (145 mg, 1.0 mmol), 5-phenyl-2-furaldehyde 4 (172 mg, 1.0 mmol) and sodium acetate (410 mg, 5.0 mmol) was added acetic acid (5 mL). The reaction mixture was refluxed for 30 h, then the excess solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), then washed with water (2×20 mL). The organic layer was dried with brine and MgSO4, then concentrated in vacuo. The desired product 5 (JL101) was obtained by recrystallization from an ethyl acetate/hexanes mixture in 45% yield (135 mg, light yellow needles). 1H NMR (400 MHz, CDCl3): 7.81-7.76 (m, 2H), 7.44 (dt, J=8.0, 1.6 Hz), 7.36 (t, J=6.0 Hz, 1H), 7.28 (d, J=3.6 Hz, 1H), 6.88 (d, J=3.6 Hz, 1H), 6.80 (s, 1H), 3.97 (q, J=7.2 Hz, 2H), 1.34 (t, J=7.2 Hz, 3H). The reaction mixture was refluxed for 30 h the excess solvent was removed in vacuo The residue was diluted with ethyl acetate (100 mL) washed with water (2×20 mL) The organic layer was dried with brine and MgSO4 concentrated in vacuo