반응 #51208

반응 방정식

5-acetyl-2,3-dihydrobenzo[b]furan

methyl cyanoacetate

benzylamine

acetic acid

→

title product

수율 60.1%

Methyl-(2E)-2-cyano-3-(2,3-dihydro-1-benzofuran-5-yl)-2-butenoate

수율 60.1%

용매

toluene

반응 조건

후처리

1. 1
   온도the whole refluxed in a Dean-Stark apparatus for 16 h
2. 2
   온도The reaction mixture was cooled
3. 3
   세척washed with 2N HCl (30 ml), NaHCO3 (30 ml), brine (30 ml)
4. 4
   건조dried (MgSO4)
5. 5
   기타evaporated to a yellow residue
6. 6
   기타This residue was purified by column chromatography

실험 절차

To a stirred solution of 5-acetyl-2,3-dihydrobenzo[b]furan (Aldrich) (1 g, 6.17 mmol) in toluene (60 ml) was added methyl cyanoacetate (0.60 ml, 6.78 mmol), benzylamine (0.07 ml, 0.61 mmol) and acetic acid (0.3 ml, 5.3 mmol) and the whole refluxed in a Dean-Stark apparatus for 16 h. The reaction mixture was cooled, washed with 2N HCl (30 ml), NaHCO3 (30 ml), brine (30 ml), dried (MgSO4) and evaporated to a yellow residue. This residue was purified by column chromatography using 15-20% EtOAc in pentane as eluant to provide the title product (902 mg, 60%); 1HNMR (400 MHz, CDCl3) δ: 2.65 (s, 3H), 3.25 (t, 2H), 3.9 (s, 3H), 4.6 (t, 2H), 6.8 (d, 1H), 7.25 (d, 1H), 7.8 (s, 1H); LRMS: M+NH4+, 261. (ES+).

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