prop-2-enoxymethylbenzene

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 solution of isomer A product from Step 1 (1.62 g, 4.23 mmol) in THF (50 mL) was added NaH 60% (540 mg, 13.4 mmol) followed by benzylbromide (1.5 mL, 13.4 mmol) and the reaction was stirred at 55 C overnight. The cooled mixture was poured into water, extracted with EtOAc, dried over Na2SO4 and concentrated. The residue was purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 99:1 to 50:50) to afford 1.07 g (53%) of allylbenzylether isomer A. extracted with EtOAc dried over Na2SO4 concentrated The residue was purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 99:1 to 50:50)

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

Procedure: To a solution of isomer A product from Step 1 (1.62 g, 4.23 mmol) in THF (50 mL) was added NaH 60% (540 mg, 13.4 mmol) followed by benzylbromide (1.5 mL, 13.4 mmol) and the reaction was stirred at 55 C overnight. The cooled mixture was poured into water, extracted with EtOAc, dried over Na2SO4 and concentrated. The residue was purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 99:1 to 50:50) to afford 1.07 g (53%) of allylbenzylether isomer A. extracted with EtOAc dried over Na2SO4 concentrated The residue was purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 99:1 to 50:50)

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

Procedure: 31.2 g of ethyl diazoacetate are added to a solution of 0.3 mol of allyl benzyl ether in 150 ml of ether with the aid of a push-syringe. After stirring for 16 hours, 31.2 g of ethyl diazoacetate are added again. After 24 hours the mixture is filtered. The organic phase is washed with saturated NaHCO3 solution and then treated in customary manner. Chromatography over silica gel (dichloromethane) allows the expected product to be obtained. After 24 hours the mixture is filtered The organic phase is washed with saturated NaHCO3 solution treated in customary manner to be obtained

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

Procedure: To a diethyl ether (100 mL) solution of allyl benzyl ether (11.1 g, 75.0 mmol), was added zinc copper couple (74.5 g, 33.0 mmol) while stirring at room temperature, a dimethoxyethane (100 mL) solution of trichloroacetyl chloride (43.6 mL, 375 mmol) was added dropwise, and the mixture was stirred at mom temperature for six hours. The reaction mixture was poured into ice-cooled aqueous sodium hydrogencarbonate (500 mL), extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The mixture was filtered and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=15/1). The obtained dichloro product was dissolved in methanol (200 mL), ammonium chloride (20.0 g, 375 mmol) was added and zinc powder (30.0 g, 450 mmol) was added little by little while vigorously stirring. After the reaction was completed, the insoluble matters were filtered off with Celite, the filtrate was distilled off under reduced pressure. Water was added to the residue, which was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=15/1 then 12/1) to obtain the title compound (7.20 g, 37.9 mmol). the mixture was stirred at mom temperature for six hours The reaction mixture was poured into ice- extracted with ethyl acetate dried over anhydrous magnesium sulfate The mixture was filtered the solvent in the filtrate was distilled off under reduced pressure The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate The obtained dichloro product was dissolved in methanol (200 mL) while vigorously stirring the insoluble matters were filtered off with Celite the filtrate was distilled off under reduced pressure Water was added to the residue, which was extracted with ethyl acetate dried over anhydrous magnesium sulfate The mixture was filtered the solvent in the filtrate was then distilled off under reduced pressure The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

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

Procedure: The title compound was prepared from allylbenzyl ether and 50% aqueous phosphinic acid by an analogous procedure to that described in J. Inorg. Nucl. Chem., 1965, 27, 697.

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

Procedure: To a diethyl ether (100 mL) solution of allyl benzyl ether (11.1 g, 75.0 mmol), was added zinc copper couple (74.5 g, 33.0 mmol) while stirring at room temperature, a dimethoxyethane (100 mL) solution of trichloroacetyl chloride (43.6 mL, 375 mmol) was added dropwise, and the mixture was stirred at mom temperature for six hours. The reaction mixture was poured into ice-cooled aqueous sodium hydrogencarbonate (500 mL), extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The mixture was filtered and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=15/1). The obtained dichloro product was dissolved in methanol (200 mL), ammonium chloride (20.0 g, 375 mmol) was added and zinc powder (30.0 g, 450 mmol) was added little by little while vigorously stirring. After the reaction was completed, the insoluble matters were filtered off with Celite, the filtrate was distilled off under reduced pressure. Water was added to the residue, which was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=15/1 then 12/1) to obtain the title compound (7.20 g, 37.9 mmol). the mixture was stirred at mom temperature for six hours The reaction mixture was poured into ice- extracted with ethyl acetate dried over anhydrous magnesium sulfate The mixture was filtered the solvent in the filtrate was distilled off under reduced pressure The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate The obtained dichloro product was dissolved in methanol (200 mL) while vigorously stirring the insoluble matters were filtered off with Celite the filtrate was distilled off under reduced pressure Water was added to the residue, which was extracted with ethyl acetate dried over anhydrous magnesium sulfate The mixture was filtered the solvent in the filtrate was then distilled off under reduced pressure The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

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

Procedure: The title compound was prepared from allylbenzyl ether and 50% aqueous phosphinic acid by an analogous procedure to that described in J. Inorg. Nucl. Chem., 1965, 27, 697.

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

Procedure: Sodium hydride (4.8 g, 0.2 mol, 50% dispersion in mineral oil) was added under nitrogen at room temperature to benzyl alcohol (21.6 g., 0.2 mol) in 150 ml. of dry dimethylformamide. The suspension was stirred at room temperature for 30 minutes and then heated at 60° C. for 30 minutes. Allyl bromide (24.2 g., 0.2 mol) was added to the suspension dropwise at 50° C. with stirring. The reaction mixture was heated at 90° C. for five and a half hours under nitrogen, cooled and stirred at room temperature overnight. The dimethylformamide was removed on a rotary evaporator and the resulting oil was extracted with ether, dried over sodium sulfate and the ether evaporated off. The resulting oil was purified on a silica gel column using hexane (500 ml) to remove the mineral oil, followed by methylene chloride (750 ml) to elute the desired product. Evaporation of the solvent yielded the title compound as a pale yellow liquid, 16 g., 54% yield. heated at 60° C. for 30 minutes with stirring The reaction mixture was heated at 90° C. for five and a half hours under nitrogen cooled stirred at room temperature overnight The dimethylformamide was removed on a rotary evaporator the resulting oil was extracted with ether dried over sodium sulfate the ether evaporated off The resulting oil was purified on a silica gel column to remove the mineral oil to elute the desired product Evaporation of the solvent

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

Procedure: In 870 g of tetrahydrofuran were dissolved 218 g (2 mol) of benzyl alcohol and 224 g (2 mol) of potassium t-butoxide. With stirring at room temperature, 242 g (2 mol) of allyl bromide was added dropwise so that the temperature might not exceed 60° C. At the end of addition, the solution was heated at 60° C. on an oil bath and ripened for one hour at the temperature. The solution was allowed to cool down to room temperature, and 11.2 g (0.1 mol) of potassium t-butoxide was added. With stirring at room temperature, 12.1 g (0.1 mol) of allyl bromide was added dropwise. The solution was heated at 60° C. on an oil bath and ripened for one hour at the temperature. The solution was cooled in an ice bath, and 550 g of water was added. The organic layer was collected. The solvent was distilled off in vacuum, yielding 299 g of a crude end product. The product was used -in the subsequent reaction without further purification. exceed 60° C At the end of addition the solution was heated at 60° C. on an oil bath to cool down to room temperature With stirring at room temperature The solution was heated at 60° C. on an oil bath ripened for one hour at the temperature The solution was cooled in an ice bath The organic layer was collected The solvent was distilled off in vacuum yielding 299 g of a crude end product the subsequent reaction without further purification

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

Procedure: The title compound was prepared from allylbenzyl ether and 50% aqueous phosphinic acid by an analogous procedure to that described in J. Inorg. Nucl. Chem., 1965, 27, 697.