반응 #2467971

반응 방정식

sodium methoxide

methyl thioglycolate

sodium methoxide

3-chloro-3-phenylprop-2-enenitrile

water

→

solid

수율 62.9%

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

수율 62.9%

용매

methanol

methanol

methanol

DMF

반응 조건

후처리

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
   기타was allowed to rt
5. 5
   workup.STIRRINGstirred for 15 min
6. 6
   추출The solution was extracted with chloroform (3×100 mL)
7. 7
   세척the combined chloroform layer was washed with water, brine
8. 8
   건조dried over sodium sulfate
9. 9
   여과The solution was filtered
10. 10
    기타evaporated the solvent
11. 11
    기타The residue was chromatographed over silica gel

실험 절차

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)+.

출처