3-methyl-1-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: To a time-dried flask containing a near-solution of 650 mg of 4-hydroxycoumarin and 800 mg of 3-methyl-1-phenylbutan-1-ol of Preparation 16 in 25 mL of dioxane under an argon atmosphere is added 2.5 mL of boron trifluoride etherate. The resulting yellow solution is left to stir at room temperature. After 3 days the volatiles are removed and the residue is partioned between diethyl ether and 1N sodium hydroxide. The basic aqueous phase is washed with diethyl ether and acidified to pH=1 with 6N hydrochloric acid. The resulting precipitant is repeatedly extracted with dichloromethane (methanol-chloroform Co-solvents). The combined dichloromethane extracts are washed once with dilute sodium bicarbonate to remove most of the unreacted 4-hydroxycoumarin, then brine, dried (magnesium sulfate), and finally concentrated under reduced pressure. The residue is adsorbed onto silica and flash column chromatographed with 30% to 40% ethyl acetate in hexane to yield 248 mg of the title product as a white solid. To a time-dried flask containing The resulting yellow solution is left After 3 days the volatiles are removed The basic aqueous phase is washed with diethyl ether The resulting precipitant is repeatedly extracted with dichloromethane (methanol-chloroform Co-solvents) The combined dichloromethane extracts are washed once with dilute sodium bicarbonate to remove most of the unreacted 4-hydroxycoumarin brine, dried (magnesium sulfate) finally concentrated under reduced pressure chromatographed with 30% to 40% ethyl acetate in hexane

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

Procedure: To a time-dried flask containing a near-solution of 650 mg of 4-hydroxycoumarin and 800 mg of 3-methyl-1-phenylbutan-1-ol of Preparation 16 in 25 mL of dioxane under an argon atmosphere is added 2.5 mL of boron trifluoride etherate. The resulting yellow solution is left to stir at room temperature. After 3 days the volatiles are removed and the residue is partioned between diethyl ether and 1N sodium hydroxide. The basic aqueous phase is washed with diethyl ether and acidified to pH=1 with 6N hydrochloric acid. The resulting precipitant is repeatedly extracted with dichloromethane (methanol-chloroform Co-solvents). The combined dichloromethane extracts are washed once with dilute sodium bicarbonate to remove most of the unreacted 4-hydroxycoumarin, then brine, dried (magnesium sulfate), and finally concentrated under reduced pressure. The residue is adsorbed onto silica and flash column chromatographed with 30% to 40% ethyl acetate in hexane to yield 248 mg of the title product as a white solid. To a time-dried flask containing The resulting yellow solution is left After 3 days the volatiles are removed The basic aqueous phase is washed with diethyl ether The resulting precipitant is repeatedly extracted with dichloromethane (methanol-chloroform Co-solvents) The combined dichloromethane extracts are washed once with dilute sodium bicarbonate to remove most of the unreacted 4-hydroxycoumarin brine, dried (magnesium sulfate) finally concentrated under reduced pressure chromatographed with 30% to 40% ethyl acetate in hexane

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

Procedure: To a time-dried flask under an argon atmosphere is added 0.50 mL of commercially available isovaleraldehyde and charged with 15 mL of diethyl ether. The solution is cooled to 0° C. and is treated with 2.0 mL (3.0 M in diethyl ether) of phenylmagnesium bromide. The reaction mixture is left to warm to room temperature overnight and then partioned between diethyl ether and saturated ammonium chloride. The aqueous phases are extracted with diethyl ether and the combined organic layers are dried (magnesium sulfate) and finally concentrated under reduced pressure. The residue is flash column chromatographed using 20% diethyl ether in hexanes to yield 800 mg of the title product as a clear, colorless oil. The reaction mixture is left to warm to room temperature overnight The aqueous phases are extracted with diethyl ether the combined organic layers are dried (magnesium sulfate) finally concentrated under reduced pressure chromatographed

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

Procedure: To a time-dried flask under an argon atmosphere is added 0.50 mL of commercially available isovaleraldehyde and charged with 15 mL of diethyl ether. The solution is cooled to 0° C. and is treated with 2.0 mL (3.0 M in diethyl ether) of phenylmagnesium bromide. The reaction mixture is left to warm to room temperature overnight and then partioned between diethyl ether and saturated ammonium chloride. The aqueous phases are extracted with diethyl ether and the combined organic layers are dried (magnesium sulfate) and finally concentrated under reduced pressure. The residue is flash column chromatographed using 20% diethyl ether in hexanes to yield 800 mg of the title product as a clear, colorless oil. The reaction mixture is left to warm to room temperature overnight The aqueous phases are extracted with diethyl ether the combined organic layers are dried (magnesium sulfate) finally concentrated under reduced pressure chromatographed