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With methylmagnesium bromide; In tetrahydrofuran; water;
REFERENCE EXAMPLE 7 2-(1-Hydroxyethyl)benzylamine A 1M solution of methylmagnesium bromide in tetrahydrofuran (12 ml, 12 mmol) was dropwise and portionwise added to a solution of 2-cyanobenzaldehyde (1.31 g, 10.0 mmol) dissolved in dried tetrahydrofuran (25 ml), followed by stirring at room temperature for one night. After the reaction, water was added to the reaction mixture followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the drying agent was filtered off, and the solution was concentrated under reduced pressure to give 1-(2-cyanophenyl)ethanol (1.47 g, quantitative). 1 H-NMR (CDCl3) delta(ppm): 1.54(3H, d, J=6.6 Hz), 5.51(1H, q, J=6.6 Hz), 7.31(1H, d, J=6.9 Hz), 7.35-7.50(2H, m), 7.83(1H, d, J=7.6 Hz).
Lithium aluminium hydride (0.758 g, 20.0 mmol) was suspended in dried tetrahydrofuran (20 ml), followed by stirring under ice-cooling in an argon atmosphere. A solution of <strong>[182964-49-4]1-(2-cyanophenyl)ethanol</strong> (1.47 g) obtained above dissolved in dried tetrahydrofuran (20 ml) was dropwise and portionwise added thereto and the reaction solution was stirred for one hour under heating at reflux. After the reaction, the solution was ice-cooled and sodium sulfate 10 hydrate was portionwise added thereto until foaming and fever ceased. The reaction solution was filtered and the filtrate was concentrated to give the title compound (1.21 g, 84%) as oily substances. This compound was used in the subsequent reaction without further purification.
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