反応 #171142

反応方程式

ethyl 2-mercaptoacetate

Compound 59

1-(3-Bromothienyl)heptanone

K2CO3

N,N-dimethylformamide

→

compound 61

収率 84.5%

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

収率 84.5%

溶媒

water

反応条件

後処理

1. 1
   抽出The organic component is extracted with ethyl acetate (3×80 mL)
2. 2
   洗浄The combined organic layers are washed with brine (2×100 mL) and water (100 mL)
3. 3
   乾燥The organic layer is then dried over MgSO4
4. 4
   その他After evaporation of the solvent
5. 5
   その他the crude compound 61 is obtained
6. 6
   その他purified by column chromatography (SiO2/5% ethyl acetate in hexanes)

実験手順

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.

出典