3,3-diphenyloxolan-2-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In anhydrous THF (80 ml) was dissolved α,α-diphenyl-γ-butyrolactone (7 g) followed by addition of lithium aluminum hydride (1 g) with ice-cooling, and the mixture was stirred under the same conditions for 3 hours. Then, under ice-cooling, a saturated aqueous solution of Rochelle salt was added dropwise to precipitate the aluminum and other inorganic matter. The supernatant was taken by decantation, dried and concentrated under reduced pressure. The residue was recrystallized from isopropyl ether to provide 2,2-diphenyl-1,4-butanediol (7 g). cooling Then, under ice-cooling to precipitate the aluminum and other inorganic matter dried concentrated under reduced pressure The residue was recrystallized from isopropyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In anhydrous THF (80 ml) was dissolved α,α-diphenyl-γ-butyrolactone (7 g) followed by addition of lithium aluminum hydride (1 g) with ice-cooling, and the mixture was stirred under the same conditions for 3 hours. Then, under ice-cooling, a saturated aqueous solution of Rochelle salt was added dropwise to precipitate the aluminum and other inorganic matter. The supernatant was taken by decantation, dried and concentrated under reduced pressure. The residue was recrystallized from isopropyl ether to provide 2,2-diphenyl-1,4-butanediol (7 g). cooling Then, under ice-cooling to precipitate the aluminum and other inorganic matter dried concentrated under reduced pressure The residue was recrystallized from isopropyl ether

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:225.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,3-Diphenyldihydrofuran-2(3H)-one (3.98 g, 16.70 mmol) and zinc chloride (0.080 g) were placed in an autoclave. Ammonia (8 mL) was added, and the reactor was sealed and heated at 225° C. for 21 hours under an argon atmosphere at an equilibrium pressure of 800 pounds per square inch. The vessel was cooled, the ammonia was vented, and a mixture of solids was obtained. The solid was treated with ethanol (100 mL), filtered and concentrated. Silica gel chromatography eluting with 5% methanol/dichloromethane gave the title compound. MS (DCI+) m/z 238.1 (M+H)+. the reactor was sealed The vessel was cooled a mixture of solids was obtained filtered concentrated Silica gel chromatography eluting with 5% methanol/dichloromethane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In anhydrous THF (80 ml) was dissolved α,α-diphenyl-γ-butyrolactone (7 g) followed by addition of lithium aluminum hydride (1 g) with ice-cooling, and the mixture was stirred under the same conditions for 3 hours. Then, under ice-cooling, a saturated aqueous solution of Rochelle salt was added dropwise to precipitate the aluminum and other inorganic matter. The supernatant was taken by decantation, dried and concentrated under reduced pressure. The residue was recrystallized from isopropyl ether to provide 2,2-diphenyl-1,4-butanediol (7 g). cooling Then, under ice-cooling to precipitate the aluminum and other inorganic matter dried concentrated under reduced pressure The residue was recrystallized from isopropyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In anhydrous THF (80 ml) was dissolved α,α-diphenyl-γ-butyrolactone (7 g) followed by addition of lithium aluminum hydride (1 g) with ice-cooling, and the mixture was stirred under the same conditions for 3 hours. Then, under ice-cooling, a saturated aqueous solution of Rochelle salt was added dropwise to precipitate the aluminum and other inorganic matter. The supernatant was taken by decantation, dried and concentrated under reduced pressure. The residue was recrystallized from isopropyl ether to provide 2,2-diphenyl-1,4-butanediol (7 g). cooling Then, under ice-cooling to precipitate the aluminum and other inorganic matter dried concentrated under reduced pressure The residue was recrystallized from isopropyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In anhydrous THF (80 ml) was dissolved α,α-diphenyl-γ-butyrolactone (7 g) followed by addition of lithium aluminum hydride (1 g) with ice-cooling, and the mixture was stirred under the same conditions for 3 hours. Then, under ice-cooling, a saturated aqueous solution of Rochelle salt was added dropwise to precipitate the aluminum and other inorganic matter. The supernatant was taken by decantation, dried and concentrated under reduced pressure. The residue was recrystallized from isopropyl ether to provide 2,2-diphenyl-1,4-butanediol (7 g). cooling Then, under ice-cooling to precipitate the aluminum and other inorganic matter dried concentrated under reduced pressure The residue was recrystallized from isopropyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,3-Diphenyldihydrofuran-2(3H)-one (1.0 g, 4.20 mmol), 2-aminoethanol (2.56 g, 42.0 mmol) and zinc chloride (0.020 g, 0.147 mmol) were heated together at 100° C. for 18 hours. The reaction was cooled, diluted with ethyl acetate, washed with water and brine, dried with MgSO4, filtered and concentrated. Silica gel chromatography eluting with 5% methanol/dichloromethane gave the title compound. MS (DCI+) m/z 282.2 (M+H)+. The reaction was cooled washed with water and brine dried with MgSO4 filtered concentrated Silica gel chromatography eluting with 5% methanol/dichloromethane

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,3-diphenyldihydrofuran-2(3H)-one (0.5 g, 2.098 mmol), 2-aminoethanol (1282 mg, 20.98 mmol) and zinc chloride (0.23 g, 1.679 mmol) was heated neat at 100° C. for 16 hours. The reaction mixture was cooled and partitioned in H2O/ethyl acetate. The organic layer was separated, dried over MgSO4, and concentrated to yield the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.32 (m, 8H), 7.23 (m, 2H), 3.81 (q, J=5.42 Hz, 2H), 3.52 (t, J=5.42 Hz, 2H), 3.45 (t, J=6.44 Hz, 2H), 2.85 (t, J=5.52 Hz, 1H), 2.79 (t, J=6.44 Hz, 2H); MS (ESI+) m/z 282 (M+H)+. The reaction mixture was cooled partitioned in H2O/ethyl acetate The organic layer was separated dried over MgSO4 concentrated