تفاعل #218362

معادلة التفاعل

3-mercapto-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

2,2′,4′-trichloroacetophenone

potassium hydroxide

ethyl acetate

→

benzothiophene

المردود 38.4%

(3-amino-5,6,7,8-tetrahydronaphtho[2,3-b]thiophen-2-yl)-(2,4-dichlorophenyl)methanone

المردود 38.4%

المذيبات

N,N-dimethylformamide

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe brown reaction mixture was cooled
2. 2
   غسيلThe organic layer was washed with water, brine
3. 3
   تجفيفdried over magnesium sulfate
4. 4
   أخرىThe solvent was removed at reduced pressure
5. 5
   أخرىthe crude product was purified on the MPLC (Biotage)
6. 6
   غسيلeluted with 30% ethyl acetate-hexane

الإجراء التجريبي

To a solution of crude 3-mercapto-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (121 mg, 0.64 mmol) and 2,2′,4′-trichloroacetophenone (143 mg, 0.64 mmol, 1.0 eq) in anhydrous N,N-dimethylformamide (5 mL) was added powdered potassium hydroxide (177 mg, 1.28 mmol, 2.0 eq). The reaction mixture was stirred under argon at 80° C. for 16 h. The brown reaction mixture was cooled and poured into ethyl acetate and water. The organic layer was washed with water, brine, and dried over magnesium sulfate. The solvent was removed at reduced pressure, and the crude product was purified on the MPLC (Biotage), eluted with 30% ethyl acetate-hexane. Trituration from hexane afforded 92.4 mg (38.4%) of the benzothiophene. 1H-NMR (Acetone-d6) δ 7.88 (broad, s, 3H), 7.62 (d, J=1.5 Hz, 1H), 7.53 (m, 2 H), 7.42 (s, 1H), 2.85 (m, 4H), 1.83 (m, 4H); MS ES (MH+=376/378); Rf=0.60 (30% ethyl acetate-hexane).

المصدر