2-(2-甲基苯基)乙醇

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2.65 g (0.019 mole) of 2-methylphenethyl alcohol in 10 ml DMF was added dropwise to a suspension of sodium hydride (1.1 g, 60% in oil; 0.08 mole) in 35 ml DMF at 0°-5° C. The suspension was stirred for 20 min under argon after which sulfamoyl chloride (2.86 g, 0.02 mole) was added portion wise at 0°-5° C. After stirring for 20 min the resultant suspension was poured into ice and extracted twice with Et2O. The combined organic phases were washed with saturated brine, dried over potassium carbonate and concentrated in vacuo to a syrup which was purified by preparative HPLC with hexane/EtOAc (1:1, v/v) as the eluant to give 1.76 g (43%) of the title compound as a solid, mp 50°-52° C. was added portion wise at 0°-5° C was poured into ice extracted twice with Et2O The combined organic phases were washed with saturated brine dried over potassium carbonate concentrated in vacuo to a syrup which was purified by preparative HPLC with hexane/EtOAc (1:1

反应条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1250 Grams of isochroman having the structure: ##STR63## 25 grams of 5% palladium-on-carbon and 12.5 grams of citric acid are placed in a 4-liter autoclave. The autoclave is sealed, heated to 150° C. and pressurized with hydrogen at 200 psig. After five hours, 12.5 grams of additional citric acid is added to the autoclave and the autoclave is resealed. The autoclave is then heated at a pressure of 200 psig and 150° C. for an additional three hours. At the end of this additional three hour period, the autoclave is opened, the contents filtered and the filtrate is distilled over 2 grams of calcium carbonate through a 24" Goodloe column yielding the following fractions: The autoclave is sealed The autoclave is then heated at a pressure of 200 psig and 150° C. for an additional three hours At the end of this additional three hour period the contents filtered the filtrate is distilled over 2 grams of calcium carbonate through a 24" Goodloe column yielding the following fractions

反应条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10 g (0.0734 mol) of 2-methylphenethyl alcohol were dissolved in 200 mL of dry CH2Cl2 under a nitrogen atmosphere; the solution was cooled to 5° C., 16.4 mL (0.1175 mol) of triethylamine were added, followed by a solution of 9.1 mL (0.1175 mol) of methanesulfonyl chloride in 100 mL of dry CH2Cl2, keeping the temperature below 15° C. The reaction mixture was allowed to warm to room temperature in 2 h, then 250 mL of water were added, the organic phase was collected and the solvent was removed in vacuo. The resulting oil was taken up in Et2O and washed with 1N HCl and successively with saturated NaHCO3 solution, the solvent was removed in vacuo, yielding 14.5 g of the title product which was used without further purification. the temperature below 15° C to warm to room temperature in 2 h the organic phase was collected the solvent was removed in vacuo washed with 1N HCl and successively with saturated NaHCO3 solution the solvent was removed in vacuo

反应条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10 g (0.0734 mol) of 2-methylphenethyl alcohol were dissolved in 200 mL of dry CH2Cl2 under a nitrogen atmosphere; the solution was cooled to 5° C., 16.4 mL (0.1175 mol) of triethylamine were added, followed by a solution of 9.1 mL (0.1175 mol) of methanesulfonyl chloride in 100 mL of dry CH2Cl2, keeping the temperature below 15° C. The reaction mixture was allowed to warm to room temperature in 2 h, then 250 mL of water were added, the organic phase was collected and the solvent was removed in vacuo. The resulting oil was taken up in Et2O and washed with 1N HCl and successively with saturated NaHCO3 solution, the solvent was removed in vacuo, yielding 14.5 g of the title product which was used without further purification. the temperature below 15° C to warm to room temperature in 2 h the organic phase was collected the solvent was removed in vacuo washed with 1N HCl and successively with saturated NaHCO3 solution the solvent was removed in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The subtitle compound (8.91 g) was prepared according to the procedure in example 5 part a using 2-(2-methylphenyl)ethanol (5.0 g), t-butylbromoacetate (5.47 ml), tetrabutylammoniumbromide (0.78 g), toluene (80 ml), 50% aqueous sodium hydroxide (40 ml), trifluoroacetic acid (20 ml) and dichloromethane (20 ml).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The subtitle compound (8.91 g) was prepared according to the procedure in example 5 part a using 2-(2-methylphenyl)ethanol (5.0 g), t-butylbromoacetate (5.47 ml), tetrabutylammoniumbromide (0.78 g), toluene (80 ml), 50% aqueous sodium hydroxide (40 ml), trifluoroacetic acid (20 ml) and dichloromethane (20 ml).

反应条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1250 Grams of isochroman having the structure: ##STR64## 25 grams of 5% palladium-on-carbon and 12.5 grams of citric acid are placed in a 4-liter autoclave. The autoclave is sealed, heated to 150° C. and pressurized with hydrogen at 200 psig. After five hours, 12.5 grams of additional citric acid is added to the autoclave and the autoclave is resealed. The autoclave is then heated at a pressure of 200 psig and 150° C. for an additional three hours. At the end of this additional three hour period, the autoclave is opened, the contents filtered and the filtrate is distilled over 2 grams of calcium carbonate through a 24" Goodloe column yielding the following fractions: The autoclave is sealed The autoclave is then heated at a pressure of 200 psig and 150° C. for an additional three hours At the end of this additional three hour period the contents filtered the filtrate is distilled over 2 grams of calcium carbonate through a 24" Goodloe column yielding the following fractions

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3 g of benzolb]furan-2-boronic acid, 3.14 g 2-bromobenzaldehyde, 0.56 g tetrakis(triphenylphosphine)-palladium (0), and 17 ml of 2N aqueous sodium carbonate in 50 ml of a 9:1 mixture of toluene-ethanol, under a nitrogen atmosphere, was heated to 100° C. for 10 h. The mixture was cooled to room temperature, diluted with 100 ml of methylene chloride and washed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give 2-(benzo[b]furan-2-yl)benzaldehyde as a brown gum, GC-M.S. (E.I.) (M/Z): 222 [M+]. The mixture was cooled to room temperature washed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia The organic layer was dried over sodium sulfate evaporated to dryness under reduced pressure

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3 g of benzolb]furan-2-boronic acid, 3.14 g 2-bromobenzaldehyde, 0.56 g tetrakis(triphenylphosphine)-palladium (0), and 17 ml of 2N aqueous sodium carbonate in 50 ml of a 9:1 mixture of toluene-ethanol, under a nitrogen atmosphere, was heated to 100° C. for 10 h. The mixture was cooled to room temperature, diluted with 100 ml of methylene chloride and washed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give 2-(benzo[b]furan-2-yl)benzaldehyde as a brown gum, GC-M.S. (E.I.) (M/Z): 222 [M+]. The mixture was cooled to room temperature washed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia The organic layer was dried over sodium sulfate evaporated to dryness under reduced pressure