(4-prop-2-enoxyphenyl)methanol

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 the product of Step A (650 mg, 3.96 mmol) in CH2Cl2 (20 mL), cooled to 0° C. under nitrogen, was added triethylamine (612 mL, 4.39 mmol) and a solution of tert-butyldimethylsilyl chloride (631 mg; 4.19 mmol) in CH2Cl2 (2 mL). After stirring at room temperature for 18 hours, the reaction mixture was diluted with ethyl acetate (60 mL), washed with water, and saturated sodium bicarbonate, and then dried (MgSO4). The filtrate was concentrated in vacuo to afford 1.1 g of the title compound which was used crude in the next reaction (Rf =0.45, 5% ethyl acetate/hexanes). washed with water, and saturated sodium bicarbonate dried (MgSO4) The filtrate was concentrated in vacuo

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

Procedure: To a solution of the product of Step A (650 mg, 3.96 mmol) in CH2Cl2 (20 mL), cooled to 0° C. under nitrogen, was added triethylamine (612 mL, 4.39 mmol) and a solution of tert-butyldimethylsilyl chloride (631 mg; 4.19 mmol) in CH2Cl2 (2 mL). After stirring at room temperature for 18 hours, the reaction mixture was diluted with ethyl acetate (60 mL), washed with water, and saturated sodium bicarbonate, and then dried (MgSO4). The filtrate was concentrated in vacuo to afford 1.1 g of the title compound which was used crude in the next reaction (Rf =0.45, 5% ethyl acetate/hexanes). washed with water, and saturated sodium bicarbonate dried (MgSO4) The filtrate was concentrated in vacuo

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

Procedure: 7.67 g (67.0 mmol) methanesulfonyl chloride were given at 0° C. to a solution of 10.0 g (60.9 mmol) (4-allyloxy-phenyl)-methanol and 9.34 ml (67.0 mmol) triethylamine in 35 ml dichloromethane and stirred at r.t. overnight. The mixture was poured in ice water, extracted with dichloromethane and the organic phase dried over Na2SO4. After removal of solvents the residue was purified by chromatography on silica gel (ethyl acetate/n-heptane 1:5) to yield 3.12 g (28%) pale yellow oil. extracted with dichloromethane the organic phase dried over Na2SO4 After removal of solvents the residue was purified by chromatography on silica gel (ethyl acetate/n-heptane 1:5) to yield 3.12 g (28%)

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

Procedure: 7.67 g (67.0 mmol) methanesulfonyl chloride were given at 0° C. to a solution of 10.0 g (60.9 mmol) (4-allyloxy-phenyl)-methanol and 9.34 ml (67.0 mmol) triethylamine in 35 ml dichloromethane and stirred at r.t. overnight. The mixture was poured in ice water, extracted with dichloromethane and the organic phase dried over Na2SO4. After removal of solvents the residue was purified by chromatography on silica gel (ethyl acetate/n-heptane 1:5) to yield 3.12 g (28%) pale yellow oil. extracted with dichloromethane the organic phase dried over Na2SO4 After removal of solvents the residue was purified by chromatography on silica gel (ethyl acetate/n-heptane 1:5) to yield 3.12 g (28%)

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

Procedure: Sodium hydride (1.20 g; 60% dispersion in oil) was added over a period of 10 minutes to a stirred solution of 4-allyloxybenzyl alcohol (4.60 g) in DHF (20 ml) at 0° C. under an atmosphere of argon. After 0.5 hours, a solution of methylchloroacetate (3.30 g) in DMF (10 ml) was added over a period of 0.25 hours. The reaction mixture was stirred for 40 hours at ambient temperature. Water (300 ml) was added and the mixture extracted with ethyl acetate (3×100 ml). The ethyl acetate extracts were combined, washed with brine (2×100 ml), dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on silica gel using a 9:1 (v/v) mixture of hexane/ethyl acetate to give 4-allyloxyphenylmethyloxy acetate (2.42 g) as a colourless oil; NMR(CDCl3): 3.75(3H,s), 4.07(2H,s), 4.52(4H,m), 5.36(2H,m), 6.10(1H,m), 6.88(2H,m) and 7.28(2H,m); m/z 236(H). the mixture extracted with ethyl acetate (3×100 ml) washed with brine (2×100 ml) dried (MgSO4) evaporated The residue was purified by flash column chromatography on silica gel using a 9:1 (v/v) mixture of hexane/ethyl acetate

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

Procedure: The compound of formula 2 (Z=trifluoromethylsulphonyloxy), methyl 3-(3-allyl-4-trifluoromethylsulphonyloxyphenyl)methyloxyacetate, was prepared as follows. Allyl bromide (4.4 g) was added to a stirred suspension of 4-hydroxybenzyl alcohol (4.34 g) and potassium carbonate (5.00 g) in butanone (40 ml). The reaction mixture was heated at reflux for 18 hours. The reaction mixture was cooled and then filtered. The filtrate was evaporated to give an oil which was purifed by flash column chromatography on silica gel using a 4:1 (v/v) mixture of hexane and ethyl acetate as eluent to give 4-allyloxybenzyl alcohol (4.50 g) as a pale yellow oil; NMR(CDCl3): 1.81(1H,t), 4.48-4.65(4H,m), 5.22-5.48(2H,m), 6.05(1H,m), 6.90(2H,m) and 7.25(2H,m), m/z 164(H). The reaction mixture was heated at reflux for 18 hours The reaction mixture was cooled filtered The filtrate was evaporated to give an oil which

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

Procedure: To a solution of the product of Step A (650 mg, 3.96 mmol) in CH2Cl2 (20 mL), cooled to 0° C. under nitrogen, was added triethylamine (612 mL, 4.39 mmol) and a solution of tert-butyldimethylsilyl chloride (631 mg; 4.19 mmol) in CH2Cl2 (2 mL). After stirring at room temperature for 18 hours, the reaction mixture was diluted with ethyl acetate (60 mL), washed with water, and saturated sodium bicarbonate, and then dried (MgSO4). The filtrate was concentrated in vacuo to afford 1.1 g of the title compound which was used crude in the next reaction (Rf =0.45, 5% ethyl acetate/hexanes). washed with water, and saturated sodium bicarbonate dried (MgSO4) The filtrate was concentrated in vacuo

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

Procedure: 7.67 g (67.0 mmol) methanesulfonyl chloride were given at 0° C. to a solution of 10.0 g (60.9 mmol) (4-allyloxy-phenyl)-methanol and 9.34 ml (67.0 mmol) triethylamine in 35 ml dichloromethane and stirred at room temperature (r.t.) overnight. The mixture was poured in ice water, extracted with dichloromethane and the organic phase dried over Na2SO4. After removal of solvents the residue was purified by chromatography on silica gel (ethyl acetate/n-heptane 1:5) to yield 3.12 g (28%) pale yellow oil. extracted with dichloromethane the organic phase dried over Na2SO4 After removal of solvents the residue was purified by chromatography on silica gel (ethyl acetate/n-heptane 1:5) to yield 3.12 g (28%)

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

Procedure: 7.67 g (67.0 mmol) methanesulfonyl chloride were given at 0° C. to a solution of 10.0 g (60.9 mmol) (4-allyloxy-phenyl)-methanol and 9.34 ml (67.0 mmol) triethylamine in 35 ml dichloromethane and stirred at room temperature (r.t.) overnight. The mixture was poured in ice water, extracted with dichloromethane and the organic phase dried over Na2SO4. After removal of solvents the residue was purified by chromatography on silica gel (ethyl acetate/n-heptane 1:5) to yield 3.12 g (28%) pale yellow oil. extracted with dichloromethane the organic phase dried over Na2SO4 After removal of solvents the residue was purified by chromatography on silica gel (ethyl acetate/n-heptane 1:5) to yield 3.12 g (28%)