benzyl 3-(2,2-dichloro-3-oxocyclobutyl)propanoate

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of benzyl 3-(2,2-dichloro-3-oxocyclobutyl)propanoate (8) (11.29 g, 37.49 mmol) in AcOH (100 ml) was treated in small portions with zinc powder (12.26 g, 187.44 mmol, 5 eq.) at RT. After addition, the reaction mixture was stirred at 80° C. for 2 h. LCMS analysis after 2 h shows complete consumption of starting material. The reaction was cooled to RT, diluted with TBME (˜100 ml), filtered and concentrated in vacuo. Heptane (250 ml) was added to remove most of the acetic acid azeotropically. Water (100 ml) was added to the resultant viscous liquid and the mixture was extracted with EtOAc (100 ml×2). The combined organic phase was washed with saturated NaHCO3 (100 ml×1), brine, dried over Na2SO4, filtered and concentrated to yield 8.12 g (93% yield at >95% purity by NMR) of 9 as a clear yellow oil. LCMS analysis on MS 19 shows 92% purity. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.30-7.43 (5 H, m), 5.14 (2 H, s), 3.08-3.21 (2 H, m), 2.64-2.76 (2 H, m), 2.34-2.48 (3 H, m), 1.96 (2 H, q, J=7.62 Hz): After addition LCMS analysis after 2 h shows complete consumption of starting material The reaction was cooled to RT diluted with TBME (˜100 ml) filtered concentrated in vacuo Heptane (250 ml) was added to remove most of the acetic acid azeotropically Water (100 ml) was added to the resultant viscous liquid the mixture was extracted with EtOAc (100 ml×2) The combined organic phase was washed with saturated NaHCO3 (100 ml×1), brine dried over Na2SO4 filtered concentrated

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of benzyl 3-(2,2-dichloro-3-oxocyclobutyl)propanoate (8) (11.29 g, 37.49 mmol) in AcOH (100 ml) was treated in small portions with zinc powder (12.26 g, 187.44 mmol, 5 eq.) at RT. After addition, the reaction mixture was stirred at 80° C. for 2 h. LCMS analysis after 2 h shows complete consumption of starting material. The reaction was cooled to RT, diluted with TBME (˜100 ml), filtered and concentrated in vacuo. Heptane (250 ml) was added to remove most of the acetic acid azeotropically. Water (100 ml) was added to the resultant viscous liquid and the mixture was extracted with EtOAc (100 ml×2). The combined organic phase was washed with saturated NaHCO3 (100 ml×1), brine, dried over Na2SO4, filtered and concentrated to yield 8.12 g (93% yield at >95% purity by NMR) of 9 as a clear yellow oil. LCMS analysis on MS 19 shows 92% purity. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.30-7.43 (5 H, m), 5.14 (2 H, s), 3.08-3.21 (2 H, m), 2.64-2.76 (2 H, m), 2.34-2.48 (3 H, m), 1.96 (2 H, q, J=7.62 Hz): After addition LCMS analysis after 2 h shows complete consumption of starting material The reaction was cooled to RT diluted with TBME (˜100 ml) filtered concentrated in vacuo Heptane (250 ml) was added to remove most of the acetic acid azeotropically Water (100 ml) was added to the resultant viscous liquid the mixture was extracted with EtOAc (100 ml×2) The combined organic phase was washed with saturated NaHCO3 (100 ml×1), brine dried over Na2SO4 filtered concentrated