2-fluoro-5-methoxybenzaldehyde

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

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

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

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 mixed solution of 2-fluoro-5-methoxybenzaldehyde (0.8 ml) in tetrahydrofuran (4 ml) and dimethylsulfoxide (4 ml), 1.97 g of trimethylsulfonium iodide and 308 mg of sodium hydride were added under ice-cooling, and the reaction solution was stirred at room temperature for 2 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50)) to afford a crude product as a colorless oil. To a solution of the crude product in tetrahydrofuran (2 ml), 200 mg of Sodium cyanoborohydride and 0.4 ml of trifluoroborane-diethylether complex were added under ice-cooling, and the reaction solution was stirred at room temperature for 2 hours. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-30/70)) to afford the title compound as a colorless oil. cooling the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50)) to afford a crude product as a colorless oil cooling the reaction solution was stirred at room temperature for 2 hours the mixture was extracted with chloroform dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-30/70))

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

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

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

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 39.4 g of methyltriphenylphosphonium iodide and 10.9 g of potassium t-butoxide were suspended in 150 ml of tetrahydrofuran. The resulting suspension was stirred at 0° C. under nitrogen stream for 30 minutes, followed by the dropwise addition thereto of a solution of 10 g of 2-fluoro-5-methoxybenzaldehyde in 20 ml of tetrahydrofuran. The resulting mixture was further stirred for one hour, quenched by the addition of water and extracted with ethyl acetate. The formed organic layer was washed with water and brine successively, dried over anhydrous magnesium sulfate, and evaporated. The resulting residue was subjected to silica gel column chromatography (developer: 5% ethyl acetate/n-hexane) to give 9.1 g of the title compound as a colorless oil. followed by the dropwise addition The resulting mixture was further stirred for one hour quenched by the addition of water extracted with ethyl acetate The formed organic layer was washed with water and brine successively dried over anhydrous magnesium sulfate evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 39.4 g of methyltriphenylphosphonium iodide and 10.9 g of potassium t-butoxide were suspended in 150 ml of tetrahydrofuran. The resulting suspension was stirred at 0° C. under nitrogen stream for 30 minutes, followed by the dropwise addition thereto of a solution of 10 g of 2-fluoro-5-methoxybenzaldehyde in 20 ml of tetrahydrofuran. The resulting mixture was further stirred for one hour, quenched by the addition of water and extracted with ethyl acetate. The formed organic layer was washed with water and brine successively, dried over anhydrous magnesium sulfate, and evaporated. The resulting residue was subjected to silica gel column chromatography (developer: 5% ethyl acetate/n-hexane) to give 9.1 g of the title compound as a colorless oil. followed by the dropwise addition The resulting mixture was further stirred for one hour quenched by the addition of water extracted with ethyl acetate The formed organic layer was washed with water and brine successively dried over anhydrous magnesium sulfate evaporated