1,1-diphenylbutane-1,4-diol

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

Procedure: 1,1-Diphenyl-1,4-butanediol (26.62 g, 0.110 mol) was dissolved in MeOH and shaken with 20% Pd/C (1.50 g) on a Parr apparatus under an H2 atmosphere (50 psi) for 17 hours. The MeOH was removed in vacuo, and the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes gave 22.53 g (91%) of desired product. The MeOH was removed in vacuo the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes

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

Procedure: 1,1-Diphenyl-1,4-butanediol (26.62 g, 0.110 mol) was dissolved in MeOH and shaken with 20% Pd/C (1.50 g) on a Parr apparatus under an H2 atmosphere (50 psi) for 17 hours. The MeOH was removed in vacuo, and the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes gave 22.53 g (91%) of desired product. The MeOH was removed in vacuo the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Butyrolactone (11.93 mL, 0.155 mol) was dissolved in anhydrous THF and cooled to 0° C. Phenylmagnesium bromide (3M in ether, 112 mL) was added dropwise over 30 minutes to the reaction under N2. After the addition, the reaction was warmed to room temperature overnight. Additional phenylmagnesium bromide (3M in ether, 103 mL) was added, and the reaction stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl (150 mL). Ether (200 mL) and 10% HCl (100 mL) were added. The organic layer was separated and washed with 10% HCl (100 mL), brine (100 mL), and then dried over MgSO4. The solution was filtered, concentrated, and the crude material chromatographed on silica gel eluting with 50% EtOAc/Hexanes to give 26.94 g (72%) of desired product as an off-white solid. After the addition the reaction was warmed to room temperature overnight The reaction was quenched with saturated NH4Cl (150 mL) Ether (200 mL) and 10% HCl (100 mL) were added The organic layer was separated washed with 10% HCl (100 mL), brine (100 mL) dried over MgSO4 The solution was filtered concentrated the crude material chromatographed on silica gel eluting with 50% EtOAc/Hexanes

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of butyrolactone (10.5 g, 122 mmol) in anhydrous THF (500 mL) was chilled to −78° C. under nitrogen atmosphere. Phenylmagnesium bromide (3M in ether, 100 mL, 300 mmol) was added via syringe at a rate that keeps the reaction temperature below −40° C. After the addition was complete, the reaction was stirred at −78° C. for two hours then the cold bath was removed and the reaction mixture was allowed to warm to room temperature overnight. The solution was then re-cooled to 10° C. on an ice bath before adding 2N aqueous ammonium chloride (200 mL) to quench the reaction. The resulting mixture was diluted with ethyl acetate (1 L) and the organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and filtered. Evaporation of solvent from the filtrate afforded crude 1,1-diphenylbutan-1,4-diol as an oil, which was purified by chromatography on silica gel, eluting with a gradient of 50% to 60% ethyl acetate in hexane. Evaporation of solvents gave a colorless solid that was triturated with hexane and collected by filtration to afford 18.2 g of pure 1,1-diphenylbutan-1,4-diol. MS (EI+): 243 (M+1); 225 (M-H2O+1). the reaction temperature below −40° C After the addition the cold bath was removed to warm to room temperature overnight The solution was then re-cooled to 10° C. on an ice bath before adding 2N aqueous ammonium chloride (200 mL) to quench the reaction the organic layer was separated washed with saturated aqueous sodium chloride dried over anhydrous sodium sulfate filtered Evaporation of solvent from the filtrate afforded crude 1,1-diphenylbutan-1,4-diol as an oil, which was purified by chromatography on silica gel eluting with a gradient of 50% to 60% ethyl acetate in hexane Evaporation of solvents gave a colorless solid that was triturated with hexane collected by filtration

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

Procedure: 1,1-Diphenyl-1,4-butanediol (26.62 g, 0.110 mol) was dissolved in MeOH and shaken with 20% Pd/C (1.50 g) on a Parr apparatus under an H2 atmosphere (50 psi) for 17 hours. The MeOH was removed in vacuo, and the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes gave 22.53 g (91%) of desired product. The MeOH was removed in vacuo the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Butyrolactone (11.93 mL, 0.155 mol) was dissolved in anhydrous THF and cooled to 0° C. Phenylmagnesium bromide (3 M in ether, 112 mL) was added dropwise over 30 minutes to the reaction under N2. After the addition, the reaction was warmed to room temperature overnight. Additional phenylmagnesium bromide (3 M in ether, 103 mL) was added, and the reaction stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl (150 mL). Ether (200 mL) and 10% HCl (100 mL) were added. The organic layer was separated and washed with 10% HCl (100 mL), brine (100 mL), and then dried over MgSO4. The solution was filtered, concentrated, and the crude material chromatographed on silica gel eluting with 50% EtOAc/Hexanes to give 26.94 g (72%) of desired product as an off-white solid. After the addition the reaction was warmed to room temperature overnight The reaction was quenched with saturated NH4Cl (150 mL) Ether (200 mL) and 10% HCl (100 mL) were added The organic layer was separated washed with 10% HCl (100 mL), brine (100 mL) dried over MgSO4 The solution was filtered concentrated the crude material chromatographed on silica gel eluting with 50% EtOAc/Hexanes

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

Procedure: 11.2 g (46.2 mmol) of 1,1-diphenyl-1,4-butanediol was hydrogenated (45° C., 5 atm) in 100 ml of methanol in the presence of 0.5 ml of concentrated sulfuric acid and 10% palladium/carbon to obtain the title compound.

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

Procedure: 60 ml (120 mmol) of 2 M solution of phenyl magnesium bromide in THF was added dropwise to 4.33 g (50.3 mmol) of γ-butyrolactone in 60 ml of THF for the duration of 50 minutes. After stirring at room temperature overnight, a saturated aqueous ammonium chloride solution and then 2 N hydrochloric acid were added dropwise to the reaction mixture. After the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound. After the extraction with ethyl acetate the organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: 1,1-Diphenyl-1,4-butanediol (26.62 g, 0.110 mol) was dissolved in MeOH and shaken with 20% Pd/C (1.50 g) on a Parr apparatus under an H2 atmosphere (50 psi) for 17 hours. The MeOH was removed in vacuo, and the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes gave 22.53 g (91%) of desired product. The MeOH was removed in vacuo the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Butyrolactone (11.93 mL, 0.155 mol) was dissolved in anhydrous THF and cooled to 0° C. Phenylmagnesium bromide (3M in ether, 112 mL) was added dropwise over 30 minutes to the reaction under N2. After the addition, the reaction was warmed to room temperature overnight. Additional phenylmagnesium bromide (3M in ether, 103 mL) was added, and the reaction stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl (150 mL). Ether (200 mL) and 10% HCl (100 mL) were added. The organic layer was separated and washed with 10% HCl (100 mL), brine (100 mL), and then dried over MgSO4. The solution was filtered, concentrated, and the crude material chromatographed on silica gel eluting with 50% EtOAc/Hexanes to give 26.94 g (72%) of desired product as an off-white solid. After the addition the reaction was warmed to room temperature overnight The reaction was quenched with saturated NH4Cl (150 mL) Ether (200 mL) and 10% HCl (100 mL) were added The organic layer was separated washed with 10% HCl (100 mL), brine (100 mL) dried over MgSO4 The solution was filtered concentrated the crude material chromatographed on silica gel eluting with 50% EtOAc/Hexanes