反応 #2467971

反応方程式

sodium methoxide

methyl thioglycolate

sodium methoxide

3-chloro-3-phenylprop-2-enenitrile

water

→

solid

収率 62.9%

Methyl 3-amino-5-phenylthiophene-2-carboxylate

収率 62.9%

溶媒

methanol

methanol

methanol

DMF

反応条件

後処理

1. 1
   workup.STIRRINGstirred the mixture at 60° C. for 2 h
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for 2 h at 60° C
4. 4
   その他was allowed to rt
5. 5
   workup.STIRRINGstirred for 15 min
6. 6
   抽出The solution was extracted with chloroform (3×100 mL)
7. 7
   洗浄the combined chloroform layer was washed with water, brine
8. 8
   乾燥dried over sodium sulfate
9. 9
   ろ過The solution was filtered
10. 10
    その他evaporated the solvent
11. 11
    その他The residue was chromatographed over silica gel

実験手順

To a solution of methyl thioglycolate (1 g, 9.43 mmol) in methanol (5 mL) was added a solution of sodium methoxide (0.5 g, 9.43 mmol) in methanol (5 mL) and stirred for 0.5 h. To the above mixture, a solution of 3-chloro-3-phenylprop-2-enenitrile (1.22 g, 7.5 mmol) in DMF (3.5 mL) was added dropwise for 10 min at rt and stirred the mixture at 60° C. for 2 h. Then, a solution of sodium methoxide (1 g, 18.6 mmol) in methanol (10 mL) was added dropwise at rt and stirring was continued for 2 h at 60° C. The mixture was allowed to rt and poured into cold water and stirred for 15 min. The solution was extracted with chloroform (3×100 mL) and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel using hexane-ethyl acetate (92:8) as eluent to give the product as a pale yellow color solid (1.1 g, 50%), mp 130-132° C. 1H NMR (400 MHz, DMSO-d6): δ 7.62-7.65 (2H, m), 7.38-7.48 (3H, m), 7.00 (1H, s), 4.29 (2H, br s), 3.74 (3H, s); LC-MS (positive ion mode): m/z 234 (M+H)+.

出典