반응 #171142

반응 방정식

ethyl 2-mercaptoacetate

Compound 59

1-(3-Bromothienyl)heptanone

K2CO3

N,N-dimethylformamide

→

compound 61

수율 84.5%

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

수율 84.5%

용매

water

반응 조건

후처리

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

실험 절차

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.

출처