反応 #45339

反応方程式

H2O

t-butyl nitrite

[3-amino-5-(trifluoromethyl)phenyl]methanol

dimethyl disulfide

→

[3-(methylthio)-5-(trifluoromethyl)phenyl]-methanol

溶媒

CHCl3

反応条件

後処理

1. 1
   抽出The mixture was extracted with EtOAc (50 mL)
2. 2
   洗浄washed with brine (15 mL)
3. 3
   乾燥dried over Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他Purification by flash chromatography with 0% to 50% EtOAc/hexanes

実験手順

To a solution of [3-amino-5-(trifluoromethyl)phenyl]methanol (319 mg, 1.67 mmol) (Step A, Example 24) in CHCl3 (5 mL) was added dimethyl disulfide (296 μL, 3.34 mmol). Next, t-butyl nitrite (285 μL, 2.4 mmol) was added dropwise by syringe. The reaction was stirred at room temperature for two hours and then poured into H2O (15 mL). The mixture was extracted with EtOAc (50 mL), washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 0% to 50% EtOAc/hexanes afforded [3-(methylthio)-5-(trifluoromethyl)phenyl]-methanol. The [3-(methylthio)-5-(trifluoromethyl)phenyl]methanol was contaminated with minor impurities that were removed after the next step. Rf=0.53 (50% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 7.63 (s, 1H), 7.40 (s, 1H), 7.35 (s, 1H), 4.71 (s, 2H), 2.51 (s, 3H).

出典