ethyl 4-(4-hydroxyphenyl)butanoate

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

Procedure: 3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (0.020 g, 0.09 mmol) obtained in Step C of Preparation Example 8 and 4-(4-hydroxy-phenyl)-butyric acid ethyl ester (0.018 g, 0.09 mmol) obtained in Step E of Preparation Example 13 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.031 g, 94%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: 3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (0.020 g, 0.09 mmol) obtained in Step C of Preparation Example 8 and 4-(4-hydroxy-phenyl)-butyric acid ethyl ester (0.018 g, 0.09 mmol) obtained in Step E of Preparation Example 13 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.031 g, 94%). to react sequentially in the same manner as in Steps A and B of Example 1

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

Procedure: To an ice cooled solution of ethyl 4-(4-hydroxyphenyl)butanoate (16.73 g, 80.32 mmol) in 200 mL of CHCl, was added bromine (4.15 mL, 80.8 mmol). The cooling bath was removed, and the reaction stirred at room temperature for 2 hours. The reaction mixture was then washed with water and brine, dried over sodium sulfate and concentrated to give 22.3 g (96.6%) of ethyl 4-(3-bromo-4-hydroxyphenyl)butanoate as a crystalline solid. The cooling bath was removed The reaction mixture was then washed with water and brine dried over sodium sulfate concentrated

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

Procedure: 3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (0.020 g, 0.09 mmol) obtained in Step C of Preparation Example 8 and 4-(4-hydroxy-phenyl)-butyric acid ethyl ester (0.018 g, 0.09 mmol) obtained in Step E of Preparation Example 13 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.031 g, 94%). to react sequentially in the same manner as in Steps A and B of Example 1