5-cyclobutylidene-2,2-dimethyl-1,3-dioxane-4,6-dione

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: Potassium cyanide (0.12 g, 1.8 mmol) was added to a mixture of 5-cyclobutylidene-2,2-dimethyl-1,3-dioxane-4,6-dione (0.30 g, 1.5 mmol) and tetra-N-butylammonium bromide (0.049 g, 0.15 mmol) (Sigma-Aldrich, Cat. #193119) in ethanol (5.0 mL). The reaction mixture was stirred at 80° C. for 2 h. After cooled to r.t., the mixture was adjusted to pH=2 with aqueous HCl. The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in dichloromethane (0-80%) to afford the desired product (0.32 g, 94%). After cooled to r.t. The mixture was extracted with ethyl acetate (3×20 mL) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure The residue was purified by flash chromatography on a silica gel column with ethyl acetate in dichloromethane (0-80%)

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

実験手順: Potassium cyanide (0.12 g, 1.8 mmol) was added to a mixture of 5-cyclobutylidene-2,2-dimethyl-1,3-dioxane-4,6-dione (0.30 g, 1.5 mmol) and tetra-N-butylammonium bromide (0.049 g, 0.15 mmol) (Sigma-Aldrich, Cat. #193119) in ethanol (5.0 mL). The reaction mixture was stirred at 80° C. for 2 h. After cooled to r.t., the mixture was adjusted to pH=2 with aqueous HCl. The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in dichloromethane (0-80%) to afford the desired product (0.32 g, 94%). After cooled to r.t. The mixture was extracted with ethyl acetate (3×20 mL) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure The residue was purified by flash chromatography on a silica gel column with ethyl acetate in dichloromethane (0-80%)

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cyclobutanone (0.50 g, 7.1 mmol) (Aldrich, Cat. #C96001) was added to a mixture of ammonium acetate (1.1 g, 14 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (1.0 g, 7.1 mmol) (Acros Organics, Cat. #19845) in toluene (10 mL), followed by acetic acid (1.0 mL). The reaction mixture was stirred at 50° C. for 4 h. After cooled to r.t., the mixture was diluted with water, and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%) to afford the desired product (0.68, 48%). After cooled to r.t. extracted with ethyl acetate (3×20 mL) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: Potassium cyanide (0.12 g, 1.8 mmol) was added to a mixture of 5-cyclobutylidene-2,2-dimethyl-1,3-dioxane-4,6-dione (0.30 g, 1.5 mmol) and tetra-N-butylammonium bromide (0.049 g, 0.15 mmol) (Sigma-Aldrich, Cat. #193119) in ethanol (5.0 mL). The reaction mixture was stirred at 80° C. for 2 h. After cooled to r.t., the mixture was adjusted to pH=2 with aqueous HCl. The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in dichloromethane (0-80%) to afford the desired product (0.32 g, 94%). After cooled to r.t. The mixture was extracted with ethyl acetate (3×20 mL) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure The residue was purified by flash chromatography on a silica gel column with ethyl acetate in dichloromethane (0-80%)

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cyclobutanone (0.50 g, 7.1 mmol) (Aldrich, Cat. #C96001) was added to a mixture of ammonium acetate (1.1 g, 14 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (1.0 g, 7.1 mmol) (Acros Organics, Cat. #19845) in toluene (10 mL), followed by acetic acid (1.0 mL). The reaction mixture was stirred at 50° C. for 4 h. After cooled to r.t., the mixture was diluted with water, and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%) to afford the desired product (0.68, 48%). After cooled to r.t. extracted with ethyl acetate (3×20 mL) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%)