[2-(oxan-2-yloxymethyl)phenyl]methanol

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of {2-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenyl}methanol (5.52 g, 24.84 mmol) in CH2Cl2 (100 ml) was cooled to 0° C. and treated with Et3N (6.92 ml, 49.68 mmol) followed by the addition of Ts2O (8.9 g, 27.33 mmol). The reaction stirred at 0° C. for 3.5 hours. The mixture was diluted with sat. NH4Cl and extracted with CH2Cl12 (2×). The combined organic solutions were washed with water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by normal phase chromatography (10% EtOAc/hexanes—20%) to give a light brown oil (7.36 g). extracted with CH2Cl12 (2×) The combined organic solutions were washed with water dried over Na2SO4 concentrated in vacuo The crude product was purified by normal phase chromatography (10% EtOAc/hexanes—20%)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of {2-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenyl}methanol (5.52 g, 24.84 mmol) in CH2Cl2 (100 ml) was cooled to 0° C. and treated with Et3N (6.92 ml, 49.68 mmol) followed by the addition of Ts2O (8.9 g, 27.33 mmol). The reaction stirred at 0° C. for 3.5 hours. The mixture was diluted with sat. NH4Cl and extracted with CH2Cl12 (2×). The combined organic solutions were washed with water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by normal phase chromatography (10% EtOAc/hexanes—20%) to give a light brown oil (7.36 g). extracted with CH2Cl12 (2×) The combined organic solutions were washed with water dried over Na2SO4 concentrated in vacuo The crude product was purified by normal phase chromatography (10% EtOAc/hexanes—20%)

反応条件: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 1,2-benzenedimethanol (5 g, 36.19 mmol) in toluene/2,3-dihydropyran (206 ml/11 ml) at 30° C. was added 3.62 g Dowex (50WX2-100). The reaction stirred at 30° C. for 5 hours. The mixture was filtered to remove Dowex, then concentrated in vacuo and put on vacuum pump overnight w/stirring to remove 2,3-dihydropyran. The crude reaction product was purified by normal phase chromatography (20% EtOAc/hexanes—25% -30%) to give a clear liquid (5.72 g). The mixture was filtered to remove Dowex concentrated in vacuo put on vacuum pump overnight w/stirring to remove 2,3-dihydropyran The crude reaction product was purified by normal phase chromatography (20% EtOAc/hexanes—25% -30%)

反応条件: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 1,2-benzenedimethanol (5 g, 36.19 mmol) in toluene/2,3-dihydropyran (206 ml/11 ml) at 30° C. was added 3.62 g Dowex (50WX2-100). The reaction stirred at 30° C. for 5 hours. The mixture was filtered to remove Dowex, then concentrated in vacuo and put on vacuum pump overnight w/stirring to remove 2,3-dihydropyran. The crude reaction product was purified by normal phase chromatography (20% EtOAc/hexanes—25% -30%) to give a clear liquid (5.72 g). The mixture was filtered to remove Dowex concentrated in vacuo put on vacuum pump overnight w/stirring to remove 2,3-dihydropyran The crude reaction product was purified by normal phase chromatography (20% EtOAc/hexanes—25% -30%)