4-CHLORO-3-HYDROXY-BENZOIC ACID METHYL ESTER

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: g (5.36 mmol) of 4-Chloro-3-hydroxy-benzoic acid methyl ester was dissolved in 40 ml of anhydrous tetrahydrofuran. To this solution was added 0.923 g (5.9 mmol) of 2-(4-chloro-phenyl)-ethanol, 5.35 g (equivalent to 16.1 mmol PPh3) of triphenylphosphine derivatized polystyrene and 2.80 g (16.1 mmol) of DEAD. The solution was shaken for 16 h at RT. The polymer was filtered off and washed with ethyl acetate. The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5). Yield 1.6 g. LC-MS (ES+): m/e=325 (M)+ The polymer was filtered off washed with ethyl acetate The solvent was removed under reduced pressure the solution was washed three times with water The organic phase was dried with magnesium sulphate filtered the solvent was removed under reduced pressure The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5)

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

Procedure: g (5.36 mmol) of 4-Chloro-3-hydroxy-benzoic acid methyl ester was dissolved in 40 ml of anhydrous tetrahydrofuran. To this solution was added 0.897 g (5.9 mmol) of 2-(4-Methoxy-phenyl)-ethanol, 5.35 g (equivalent to 16.1 mmol PPh3) of triphenylphosphine derivatized polystyrene and 2.80 g (16.1 mmol) of DEAD. The solution was shaken for 16 h at RT. The polymer was filtered off and washed with ethyl acetate. The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5). The polymer was filtered off washed with ethyl acetate The solvent was removed under reduced pressure the solution was washed three times with water The organic phase was dried with magnesium sulphate filtered the solvent was removed under reduced pressure The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5)

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

Procedure: 2.0 g (10.72 mmol) of 4-Chloro-3-hydroxy-benzoic acid methyl ester was dissolved in 20 ml of anhydrous tetrahydrofuran. To this solution was added 2.25 g (11.79 mmol) of 2-(2,4-Dichlorophenyl)-ethanol, 10.71 g (equivalent to 32.2 mmol PPh3) of triphenylphosphine derivatized polystyrene and 5.6 g (32.2 mmol) of DEAD. The solution was shaken for 16 h at RT. The polymer was filtered off and washed with ethyl acetate. The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/6). The polymer was filtered off washed with ethyl acetate The solvent was removed under reduced pressure the solution was washed three times with water The organic phase was dried with magnesium sulphate filtered the solvent was removed under reduced pressure The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/6)

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

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 4-chloro-3-hydroxybenzoate [Chem. Pharm. Bull. 1994, 42(11),2365-9] (0.73 g), caesium carbonate (1.27 g) and tert butylbromoacetate (0.58 mL) in DMF (6 mL) were heated and stirred at 60° C. for 3 h. Water was added and the product was extracted into ethyl acetate. The extracts were dried over sodium sulphate, filtered and the solvent was evaporated. The resulting oil was purified by flash chromatography, using 1:10 ethyl acetate/isohexane as eluent, to yield the subtitle compound as a colourless oil (1.25 g). the product was extracted into ethyl acetate The extracts were dried over sodium sulphate filtered the solvent was evaporated The resulting oil was purified by flash chromatography

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 4-chloro-3-hydroxybenzoate [Chem. Pharm. Bull. 1994, 42(11),2365-9] (0.73 g), caesium carbonate (1.27 g) and tert butylbromoacetate (0.58 mL) in DMF (6 mL) were heated and stirred at 60° C. for 3 h. Water was added and the product was extracted into ethyl acetate. The extracts were dried over sodium sulphate, filtered and the solvent was evaporated. The resulting oil was purified by flash chromatography, using 1:10 ethyl acetate/isohexane as eluent, to yield the subtitle compound as a colourless oil (1.25 g). the product was extracted into ethyl acetate The extracts were dried over sodium sulphate filtered the solvent was evaporated The resulting oil was purified by flash chromatography

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 4-chloro-3-hydroxybenzoate [Chem. Pharm. Bull. 1994, 42(11),2365-9] (0.73 g), caesium carbonate (1.27 g) and tert butylbromoacetate (0.58 mL) in DMF (6 mL) were heated and stirred at 60° C. for 3 h. Water was added and the product was extracted into ethyl acetate. The extracts were dried over sodium sulphate, filtered and the solvent was evaporated. The resulting oil was purified by flash chromatography, using 1:10 ethyl acetate/isohexane as eluent, to yield the subtitle compound as a colourless oil (1.25 g). the product was extracted into ethyl acetate The extracts were dried over sodium sulphate filtered the solvent was evaporated The resulting oil was purified by flash chromatography

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

Procedure: g (5.36 mmol) of 4-Chloro-3-hydroxy-benzoic acid methyl ester was dissolved in 40 ml of anhydrous tetrahydrofuran. To this solution was added 0.923 g (5.9 mmol) of 2-(4-chloro-phenyl)-ethanol, 5.35 g (equivalent to 16.1 mmol PPh3) of triphenylphosphine derivatized polystyrene and 2.80 g (16.1 mmol) of DEAD. The solution was shaken for 16 h at RT. The polymer was filtered off and washed with ethyl acetate. The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5). Yield 1.6 g. LC-MS (ES+): m/e=325 (M)+ The polymer was filtered off washed with ethyl acetate The solvent was removed under reduced pressure the solution was washed three times with water The organic phase was dried with magnesium sulphate filtered the solvent was removed under reduced pressure The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5)

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

Procedure: g (5.36 mmol) of 4-Chloro-3-hydroxy-benzoic acid methyl ester was dissolved in 40 ml of anhydrous tetrahydrofuran. To this solution was added 0.897 g (5.9 mmol) of 2-(4-Methoxy-phenyl)-ethanol, 5.35 g (equivalent to 16.1 mmol PPh3) of triphenylphosphine derivatized polystyrene and 2.80 g (16.1 mmol) of DEAD. The solution was shaken for 16 h at RT. The polymer was filtered off and washed with ethyl acetate. The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5). The polymer was filtered off washed with ethyl acetate The solvent was removed under reduced pressure the solution was washed three times with water The organic phase was dried with magnesium sulphate filtered the solvent was removed under reduced pressure The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5)