3-methyl-3-phenylbutan-1-ol

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: 3-Metyl-3-phenylbutanol (0.82 g) was refluxed in 47% hydrobromic acid (5 ml) under heating for 7 hours. To the reaction solution was added water and the solution was extracted with ether. After washing with a saturated aqueous solution of sodium chloride, the ether layer was dried over anhydrous magnesium sulfate, and the residue was then subjected to silica gel column chromatography. Elution with a hexane - ethyl acetate 10:1) mixture gave 1.02 of 1-bromo-3-methyl-3-phenylbutane. under heating for 7 hours the solution was extracted with ether After washing with a saturated aqueous solution of sodium chloride the ether layer was dried over anhydrous magnesium sulfate Elution with a hexane - ethyl acetate 10:1) mixture

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

Procedure: 3-Metyl-3-phenylbutanol (0.82 g) was refluxed in 47% hydrobromic acid (5 ml) under heating for 7 hours. To the reaction solution was added water and the solution was extracted with ether. After washing with a saturated aqueous solution of sodium chloride, the ether layer was dried over anhydrous magnesium sulfate, and the residue was then subjected to silica gel column chromatography. Elution with a hexane - ethyl acetate 10:1) mixture gave 1.02 of 1-bromo-3-methyl-3-phenylbutane. under heating for 7 hours the solution was extracted with ether After washing with a saturated aqueous solution of sodium chloride the ether layer was dried over anhydrous magnesium sulfate Elution with a hexane - ethyl acetate 10:1) mixture

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

Procedure: 3-Methyl-3-phenylbutanoic acid (0.90 9) was dropwise added to a suspension of lithium alminum hydride (0.2 g) in 15 ml of tetrahydrofuran at room temperature and the mixture was stirred for 30 minutes. To the reaction mixture was added a saturated aqueous solution of sodium bicarbonate under ice cooling, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride,, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (20 g). Elution with a hexane ethyl acetate (5:1) mixture gave 0.75 g of 3-metyl-3-phenylbutanol. the reaction solution was extracted with ethyl acetate The organic layer was washed with a saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate concentrated under reduced pressure Elution with a hexane ethyl acetate (5:1) mixture

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

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

Procedure: Step B To a solution of oxalyl chloride (1.7 g, 13 mmol) (Aldrich) in dichloromethane (50 mL) at −78° C. was added the solution of dimethyl sulfoxide (1.9 mL, 27 mmol) in dichloromethane (10 mL) dropwise. After 5 mins, the solution of 3-methyl-3-phenyl-butan-1-ol (2 g, 12 mmol) in dichloromethane (10 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 15 min. Triethylamine (6.1 mL, 44 mol) was added and the reaction mixture was slowly warmed up to room temperature and stirred at room temperature for 45 min. The water was added. The organic layers were separated, and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with 10% of HCl, saturated NaHCO3, brine, dried over MgSO4, and concentrated to give 3-methyl-3-phenyl-butyraldehyde as a colorless oil (Yield: 1.8 g, 90%). the reaction mixture was slowly warmed up to room temperature stirred at room temperature for 45 min The organic layers were separated the aqueous layer was extracted with dichloromethane washed with 10% of HCl, saturated NaHCO3, brine dried over MgSO4 concentrated

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

Procedure: Step A To a solution of 3-methyl-3-phenylbutanoic acid (ChemBridge) (4.46 g, 25 mmol) in anhydrous tetrahydrofuran (150 mL) at 0° C. was added a tetrahydrofuran solution (1 M) of BH3.THF (Aldrich, 50 mL, 50 mmol) under nitrogen. The reaction mixture was stirred at room temperature for 3 h, then concentrated. The residue was partitioned between ethyl acetate and water. The organic layer were separated, washed with water, aqueous HCl solution, brine, dried over MgSO4, and concentrated to give 3-methyl-3-phenyl-butan-1-ol as a colorless oil (4.1 g, 100%). concentrated The residue was partitioned between ethyl acetate and water The organic layer were separated washed with water, aqueous HCl solution, brine dried over MgSO4 concentrated

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

Procedure: To a suspension of lithium aluminum hydride (8.62 g, 228 mmol) in tetrahydrofuran (200 ml) was added dropwise a solution of 3-methyl-3-phenylbutanoic acid (20.26 g, 113.7 mmol) in tetrahydrofuran (100 ml) under ice-cooling, and the mixture was stirred overnight at room temperature. After ice-cooling the reaction solution, water (8 ml), 15% aqueous sodium hydroxide solution (8 ml) and water (20 ml) were successively added dropwise to decompose excess lithium aluminum hydride. The mixture was stirred as it was at room temperature for 2 hrs. The resulting precipitate was removed by filtration, and the precipitate was washed with ethyl acetate. The solvent of the recovered filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the objective substance. cooling were successively added dropwise The mixture was stirred as it was at room temperature for 2 hrs The resulting precipitate was removed by filtration the precipitate was washed with ethyl acetate The solvent of the recovered filtrate was evaporated under reduced pressure The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the objective substance

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

Procedure: 3-Metyl-3-phenylbutanol (0.82 g) was refluxed in 47% hydrobromic acid (5 ml) under heating for 7 hours. To the reaction solution was added water and the solution was extracted with ether. After washing with a saturated aqueous solution of sodium chloride, the ether layer was dried over anhydrous magnesium sulfate, and the residue was then subjected to silica gel column chromatography. Elution with a hexane - ethyl acetate 10:1) mixture gave 1.02 of 1-bromo-3-methyl-3-phenylbutane. under heating for 7 hours the solution was extracted with ether After washing with a saturated aqueous solution of sodium chloride the ether layer was dried over anhydrous magnesium sulfate Elution with a hexane - ethyl acetate 10:1) mixture

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

Procedure: 3-Methyl-3-phenylbutanoic acid (0.90 9) was dropwise added to a suspension of lithium alminum hydride (0.2 g) in 15 ml of tetrahydrofuran at room temperature and the mixture was stirred for 30 minutes. To the reaction mixture was added a saturated aqueous solution of sodium bicarbonate under ice cooling, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride,, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (20 g). Elution with a hexane ethyl acetate (5:1) mixture gave 0.75 g of 3-metyl-3-phenylbutanol. the reaction solution was extracted with ethyl acetate The organic layer was washed with a saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate concentrated under reduced pressure Elution with a hexane ethyl acetate (5:1) mixture

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