反応 #955900

反応方程式

4-hydroxythiophenol

2-bromoethanol

K2CO3

→

(a)

収率 72.0%

溶媒

dimethylformamide

—

ice water

反応条件

後処理

1. 1
   抽出extracted with dichloromethane (DCM) (3×50 ml)
2. 2
   乾燥The organic part was dried by MgSO4
3. 3
   その他solvent was removed under a rotary evaporator
4. 4
   その他The crude product was purified on silica gel column

実験手順

(FIG. 2) (a) (4-(2-hydroxyethylsulfanyl) phenol) was synthesized by a modified literature procedure (pl add ref). 4-hydroxythiophenol (mercaptophenol) (6.00 g, 47.61 mmole), 2-bromoethanol (5.90 g, 47.6 mmol) and K2CO3 (6.6 g, 47.48 mmol) was stirred in dimethylformamide (DMF, 50 ml) at −5° C. for 30 minutes. The reaction mixture was then stirred for 12 hours at room temperature. The reaction mixture was poured in ice water (300 ml) and extracted with dichloromethane (DCM) (3×50 ml). The organic part was dried by MgSO4 and then solvent was removed under a rotary evaporator. The crude product was purified on silica gel column by using a chloroform/methanol (94:6) solvent mixture. Yield: 72%. 1H NMR (CDCl3): δ, 8.01 (s, OH, 1H), 7.33 (d, 2H, J=8.7 Hz), 6.78 (d, 2H, J=8.7 Hz), 4.52 (s, OH, 1H), 3.67 (t, 2H, J=6 Hz), 2.99 (t, 2H, J=5.7).

出典