反応 #91578

反応方程式

5-chlorothiophene-2-carboxylic acid

cyclohexylmethyl bromide

potassium carbonate

→

cyclohexylmethyl 5-chlorothiophene-2-carboxylate

溶媒

water

反応条件

後処理

1. 1
   その他Reaction mixture
2. 2
   抽出extracted with hexanes three times
3. 3
   乾燥Combined organic layers were dried over anhydrous MgSO4
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他Purification by flash chromatography (2%-15% EtOAc—hexanes gradient)

実験手順

A mixture of 5-chlorothiophene-2-carboxylic acid (3.01 g, 19.0 mmol), cyclohexylmethyl bromide (3.51 g, 19.8 mmol) and potassium carbonate (2.81 g, 20.33 mmol) was stirred under Ar at +85° C. for 3 days and cooled to room temperature. Reaction mixture was diluted with water and extracted with hexanes three times. Combined organic layers were dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (2%-15% EtOAc—hexanes gradient) gave cyclohexylmethyl 5-chlorothiophene-2-carboxylate as a colorless oil. Yield (4.76 g, 97%); 1H NMR (400 MHz, CDCl3) δ 7.56-7.60 (m, 1H), 6.90-6.94 (m, 1H), 4.08 (d, J=6.10 Hz, 2H), 1.64-1.82 (m, 6H), 1.10-1.34 (m, 3H), 0.97-1.10 (m, 2H).

出典