Reacción #171142

Ecuación de reacción

ethyl 2-mercaptoacetate

Compound 59

1-(3-Bromothienyl)heptanone

K2CO3

N,N-dimethylformamide

→

compound 61

Rendimiento 84.5%

Ethyl 3-hexylthieno[3,2-b]thiophene-2-carboxylate

Rendimiento 84.5%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe organic component is extracted with ethyl acetate (3×80 mL)
2. 2
   LavadoThe combined organic layers are washed with brine (2×100 mL) and water (100 mL)
3. 3
   SecadoThe organic layer is then dried over MgSO4
4. 4
   OtroAfter evaporation of the solvent
5. 5
   Otrothe crude compound 61 is obtained
6. 6
   Otropurified by column chromatography (SiO2/5% ethyl acetate in hexanes)

Procedimiento

Compound 59 (35.4 g, 0.13 mol) and K2CO3 (27.6 g, 0.2 mol) are mixed with N,N-dimethylformamide (100 mL). A catalytic amount (˜25 mg) 18-crown-6 is added, and to this mixture, ethyl 2-mercaptoacetate (14.0 mL, 0.13 mol) is added dropwise at 60° C. The mixture is stirred overnight and poured into water (500 mL). The organic component is extracted with ethyl acetate (3×80 mL). The combined organic layers are washed with brine (2×100 mL) and water (100 mL). The organic layer is then dried over MgSO4. After evaporation of the solvent, the crude compound 61 is obtained and purified by column chromatography (SiO2/5% ethyl acetate in hexanes) to yield pure compound 61 (32.1 g, 84.5%). GC/MS: 296 g/mol (M). 1H NMR (CD2Cl2): δ 7.56 (d, 1H), 7.24 (d, 1H), 4.34 (q, 2H), 3.15 (t, 2H), 1.71 (m, 2H), 1.32 (m, 6H), 0.88 (m, 6H). 13C NMR: 163.24, 143.31, 141.85, 141.09, 131.13, 128.44, 120.35, 61.25, 31.99, 29.72 (overlap), 22.98, 14.52, 14.23.

Fuente