4-iodobutyl acetate

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

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diisopropylamine (8.25 ml) was dissolved in anhydrous tetrahydrofuran (100 ml) under an argon atmosphere, and the solution was cooled at -70° C. 1.6M n-butyllithium hexane solution (37 ml, 60 mmole) was added dropwise to the solution, to which a solution of ethyl isobutyrate (5.6 g, 48 mmole) in anhydrous tetrahydrofuran (5 ml) was then added, while maintaining the reaction temperature at not higher than -60° C. After stirring was continued for 30 minutes under the same reaction conditions, a solution of 4-acetoxybutyl iodide (12 g, 50 mmole) in hexamethylphosphortriamide (5 ml) was added dropwise to the reaction solution, and the reaction was allowed to proceed until the mixture rose to room temperature. After the completion of the reaction, 2N hydrochloric acid (10 ml) was added, and the mixture was concentrated under reduced pressure. The resulting product was dissolved in ethyl acetate (100 ml), and the organic layer was washed with water, dried and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel using isopropyl ether to give ethyl 6-acetoxy-2,2-dimethylhexanoate (5.6 g, 50%). was then added while maintaining the reaction temperature at not higher than -60° C was continued for 30 minutes under the same reaction conditions rose to room temperature was added the mixture was concentrated under reduced pressure The resulting product was dissolved in ethyl acetate (100 ml) the organic layer was washed with water dried concentrated under reduced pressure The residue was chromatographed on a column of silica gel

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

Procedure: 10 mmol (1.43 g) lepidine and 10 mmol (2.42 g) 4-iodobutylacetate are heated 4 h at 120° C. and after cooling repeatedly stirred with ether, decanted a finally dried in vacuum. after cooling repeatedly decanted a finally dried in vacuum

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

Procedure: 10 mmol (0.93 g) γ-picoline and 10 mmol (2.42 g) 4-iodobutylacetate are heated 4 h at 120° C. and after cooling repeatedly stirred with ether, decanted a finally dried in vacuum. after cooling repeatedly decanted a finally dried in vacuum

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

Procedure: 10 mmol (1.49 g) 2-methyl-benzothiazole and 10 mmol (2.42 g) 4-iodobutylacetate are heated for 4 h at 120° C. and after cooling mixed with ether sucked off, again washed with ether and dried in vacuum. after cooling again washed with ether dried in vacuum

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

Procedure: 10 mmol (1.49 g) 2-methyl-benzothiazole and 10 mmol (2.42 g) 4-iodobutylacetate are heated for 4 h at 120° C. and after cooling mixed with ether sucked off, again washed with ether and dried in vacuum. after cooling again washed with ether dried in vacuum

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

Procedure: 10 mmol (1.49 g) 2-methyl-benzothiazole and 10 mmol (2.42 g) 4-iodobutylacetate are heated for 4 h at 120° C. and after cooling mixed with ether sucked off, again washed with ether and dried in vacuum. after cooling again washed with ether dried in vacuum

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl 4-bromo-3-hydroxybenzoate (200 mg) was dissolved in DMF (10 ml) and 4-iodo-butyl acetate (195 μl) and sodium hydride (56 mg, 60% dispersion in mineral oil) were added and the reaction stirred at 80° C. under nitrogen for 3 hours. The reaction was quenched with water (5 ml) and the solvents evaporated under vacuum. The residue was partitioned between ethyl acetate/chloroform (1:1) and water. The organic phase was dried using a hydrophobic filter and the solvent evaporated in vacuo to give ethyl 3-{[4-(acetyloxy)butyl]oxy}-4-bromobenzoate as a yellow gel (318 mg). The reaction was quenched with water (5 ml) the solvents evaporated under vacuum The residue was partitioned between ethyl acetate/chloroform (1:1) and water The organic phase was dried a hydrophobic filter the solvent evaporated in vacuo

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diisopropylamine (8.25 ml) was dissolved in anhydrous tetrahydrofuran (100 ml) under an argon atmosphere, and the solution was cooled at -70° C. 1.6M n-butyllithium hexane solution (37 ml, 60 mmole) was added dropwise to the solution, to which a solution of ethyl isobutyrate (5.6 g, 48 mmole) in anhydrous tetrahydrofuran (5 ml) was then added, while maintaining the reaction temperature at not higher than -60° C. After stirring was continued for 30 minutes under the same reaction conditions, a solution of 4-acetoxybutyl iodide (12 g, 50 mmole) in hexamethylphosphortriamide (5 ml) was added dropwise to the reaction solution, and the reaction was allowed to proceed until the mixture rose to room temperature. After the completion of the reaction, 2N hydrochloric acid (10 ml) was added, and the mixture was concentrated under reduced pressure. The resulting product was dissolved in ethyl acetate (100 ml), and the organic layer was washed with water, dried and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel using isopropyl ether to give ethyl 6-acetoxy-2,2-dimethylhexanoate (5.6 g, 50%). was then added while maintaining the reaction temperature at not higher than -60° C was continued for 30 minutes under the same reaction conditions rose to room temperature was added the mixture was concentrated under reduced pressure The resulting product was dissolved in ethyl acetate (100 ml) the organic layer was washed with water dried concentrated under reduced pressure The residue was chromatographed on a column of silica gel