Tetrahydrofuran → [2-(Propan-2-ylamino)phenyl]methanol
反応式
[CH3:1][C:2]1([CH3:12])[NH:7][CH2:6][C:5]2C=CC=C[C:4]=2O1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:19]1[CH2:23][O:22][CH2:21][CH2:20]1>>[CH:2]([NH:7][C:6]1[CH:5]=[CH:4][CH:21]=[CH:20][C:19]=1[CH2:23][OH:22])([CH3:12])[CH3:1]参加物
4
実験手順
A solution of 2,2,-dimethyl-1,4-dihydro-2H-benzo[1,3]oxazine (125 g, 0.77 mol) in THF (1 L) was filtered through a scintillation funnel and then added dropwise via an addition funnel, over a period of 2.5 h, to a stirred solution of 1.0 M LiAlH4 in THF (800 mL) at 0° C. The reaction was quenched by slow portionwise addition of Na2SO4.10H2O (110 g), over a period of 1.5 h, at 0° C. The reaction mixture was stirred overnight, filtered and the solid salts were washed thoroughly with THF. The filtrate was concentrated under reduced pressure to yield 2-isopropylaminophenylmethanol (120 g, 95%) as a yellow oil. 1H NMR (CDCl3; 300 MHz): 1.24 (d, 6H, CH(CH3)2), 3.15 (bs, 1H, OH), 3.61 (sept, 1H, CH(CH3)2), 4.57 (s, 2H, CH2), 6.59 (t, 1H, ArH), 6.65 (d, 1H, ArH), 6.99 (d, 1H, ArH), 7.15 (t, 1H, ArH).