反応 #462276

反応方程式

3-aminobenzyl alcohol

tert-butyldimethylsilyl chloride

triethylamine

→

3-(O-t-butyldimethylsilyloxymethyl)aniline

収率 57.0%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他was then partitioned between ethyl acetate and H2O
2. 2
   洗浄The organic phase was washed twice with H2O, twice with brine
3. 3
   乾燥dried over MgSO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo

実験手順

To a solution of 3-aminobenzyl alcohol (2.00 g, 16.2 mmol) and tert-butyldimethylsilyl chloride (2.90 g, 19.4 mmol) in CH2Cl2 (32.5 mL) was added triethylamine (7.45 mL, 53.5 mmol). The reaction mixture was stirred for 18 hours at ambient temperature and was then partitioned between ethyl acetate and H2O. The organic phase was washed twice with H2O, twice with brine, dried over MgSO4, filtered, and concentrated in vacuo. 3-(O-t-butyldimethylsilyloxymethyl)aniline (2.18 g, 57%) was obtained as a yellow oil by chromatography on silica gel (30% ethyl acetate/hexane). 1H NMR (300 MHz, CDCl3) δ7.10 (1H, t, J=7.5 Hz), 6.67-6.72 (2H, m), 6.56 (1H, br d, J=7.5 Hz), 4.66 (2H, s), 3.63 (2H, br s), 0.94 (9H, s), 0.09 (6H, s). MS m/e 238 (M+H)+, 255 (M+NH4)30 .

出典