4-butoxyphenol

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: 6.1 g of 4-(6-methacryloyloxyhexyloxy)benzoic acid were converted to the acid chloride in a manner similar to example 6. This substance was taken up in 100 ml of tetrahydrofuran (THF) and added dropwise at 0° to 5° C. to a stirred solution of 3.3 g of hydroquinone monobutyl ether in 100 ml of THF and 4 ml of triethylamine. The mixture was stirred for a further 3 hours at room temperature and the triethylamine hydrochloride was then filtered out. The filtrate was evaporated to dryness and the residue dissolved in 50 ml of dichloromethane. The solution was washed several times with water, dried with sodium sulphate and the solvent then distilled off. The crude product so obtained was purified by column chromatography and recrystallisation from n-hexane. the triethylamine hydrochloride was then filtered out The filtrate was evaporated to dryness the residue dissolved in 50 ml of dichloromethane The solution was washed several times with water dried with sodium sulphate the solvent then distilled off

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

Procedure: 30.0 g of PPE, 5.00 g (28.1 mmol) of the compound (12) and 4.40 g (28.9 mmol) of p-butoxyphenol were dissolved in 100 ml of chloroform under an argon gas atmosphere and the whole was stirred at room temperature overnight. After addition of water to the reaction mixture, the whole was extracted with methylene chloride. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography to obtain 8.30 g of p-butoxyphenyl p-allyloxybenzoate (13) (yield: 94.6%). the whole was extracted with methylene chloride After removal of the solvent by distillation the residue was purified by silica gel column chromatography

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100 mg (0.21 mmol) 7-(4-bromophenyl)-4-ethoxy-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d′]dipyrimidine, 51 mg (0.31 mmol) 4-n-butoxyphenol, 134 mg (0.41 mmol) Cs2CO3, 1 μl (5 mole %) ethyl acetate and 1.5 mg (5 mole %) CuBr were suspended in 5 ml absolute toluene and heated in a microwave oven at 180° C. for 17 h. Thereafter, the solvent was removed and the residue was purified by means of flash chromatography. 4 mg (3%) of the title substance is obtained. ESI-MS [m/z]: 571 Thereafter, the solvent was removed the residue was purified by means of flash chromatography 4 mg (3%) of the title substance is obtained

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

Procedure: (2S)-3-[4-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester from Example 173, Step A was treated with 4-Butoxy-phenol under the Standard Procedure J. The compound thus obtained was allowed to react under Standard hydrolysis procedure C (NaOH) to give the title compound. MS(ES) for C23H30O6 [M+NH4]+: 420, [M+Na]+: 425, [M+H]+: 403. The compound thus obtained

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

Procedure: The title compound was prepared from 3-[4-(3-Bromo-propoxy)-3-methoxy-phenyl]-2-methoxy-propionic acid (Example 175, Step B) and 4-Butoxy-phenol following the Standard Procedure J. MS (ES) for C24H32O7 [M+Na]+: 455.

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

Procedure: The title compound was prepared from 3-[4-(3-Bromo-propoxy)-3-methoxy-phenyl]-2-methoxy-propionic acid (Example 175, Step B) and 4-Butoxy-phenol following the Standard Procedure J. MS (ES) for C24H32O7 [M+Na]+: 455.

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

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

Procedure: First, 2-(4-butoxyphenoxy)benzoic acid was prepared. A stirred mixture of 2-chlorobenzoic acid (10.0 g, 64 mmol), 4-butoxyphenol (12.7 g, 77 mmol), potassium carbonate (17.6 g, 128 mmol), copper powder (0.24 g, 3.8 mmol), copper (I) iodide (0.20 g, 1.3 mmol), dithioerithritol (0.20 g, 1.3 mmol), and 75 mL of N,N-dimethylformamide was heated at reflux for 5 h and then cooled to ambient. The reaction mixture was poured onto a mixture of 300 g of ice plus 100 mL of 10% aqueous HCl. The precipitated product was extracted into diethyl ether. The product was purified by extraction into 5% aqueous NaOH, followed by acidification with concentrated HCl. The precipitate was collected, washed with water, and dried in vacuo over CaSO4 to provide 8.27 g (45% of theory) of 2-(4-butoxyphenoxy)benzoic acid as a brown powder. First, 2-(4-butoxyphenoxy)benzoic acid was prepared was heated at reflux for 5 h cooled The precipitated product was extracted into diethyl ether The product was purified by extraction into 5% aqueous NaOH The precipitate was collected washed with water dried in vacuo over CaSO4

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

Procedure: The procedure described in Example 1 was repeated using 2-allylphenol (9.6 g), instead of 4-butoxyphenol, to prepare 3-(2-allylphenoxymethyl)-3-hydroxyquinuclidine which was dissolved in acetone and a solution of hydrogen chloride in ether added to afford 3-(2-allylphenoxymethyl)-3-hydroxyquinuclidine hydrochloride as a colourless solid, m.p. 102°-128° C.; microanalysis, found: C, 64.7; H, 8.0; N, 4.5% C17H23NO2.HCl.0.3H2O requires C, 64.8; H, 7.9; N, 4.4%; NMR (DMSO-d6): 1.6-1.8(1H, m), 1.7-2.0(2H, m), 2.1-2.3(2H, m), 3.0-3.5(8H, m), 4.0-4.1(2H, q), 5.0-5.1(2H, m), 5.5(1H, s), 5.9-6.1(1H, m), 6.8-7.0(2H, m), 7.1-7.3(2H, m) and 10.7(1H, br); m/z 274 (M+H).

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

Procedure: The title compound was prepared from 4-butoxy-phenol and N-methyl-N-phenylcarbamoyl chloride. The crude product was recrystallized from ethanol (22%, white crystals). HPLC-MS m/z=300.1 (M+1), Rt: 5.20. The crude product was recrystallized from ethanol (22%, white crystals)