Reacción #91578

Ecuación de reacción

5-chlorothiophene-2-carboxylic acid

cyclohexylmethyl bromide

potassium carbonate

→

cyclohexylmethyl 5-chlorothiophene-2-carboxylate

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroReaction mixture
2. 2
   Extracciónextracted with hexanes three times
3. 3
   SecadoCombined organic layers were dried over anhydrous MgSO4
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroPurification by flash chromatography (2%-15% EtOAc—hexanes gradient)

Procedimiento

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).

Fuente