Potassium Carbonate → (E)-3-[4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridin-1-yl]methylbenzo[b]furan

HRID 1490039노트

반응식

HRID 1490039 반응식
S(Cl)(Cl)=O.O[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[O:10][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[C:22]1(/[CH:28]=[CH:29]/[C:30]2[CH2:31][CH2:32][NH:33][CH2:34][CH:35]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCOCC.O>[C:22]1(/[CH:28]=[CH:29]/[C:30]2[CH2:35][CH2:34][N:33]([CH2:6][C:7]3[C:8]4[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=4[O:10][CH:11]=3)[CH2:32][CH:31]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 3666346Benzofuran-3-ylmethanolHCID 15342358(E)-4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridine

생성물 1

HCID 9953447(E)-3-[4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridin-1-yl]methylbenzo[b]furan수율 49.2%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

Thionyl chloride (0.25 ml, 3.4 mmol) was added to a solution of 3-hydroxymethylbenzo[b]furan (0.4515 g, 3.05 mmol) in anhydrous ether (10 ml), the mixture was stirred at room temperature for 2.5 hours and evaporated to dryness. The residue was dissolved in anhydrous dimethylformamide (10 ml), potassium carbonate (1.05 g, 7.60 mmol) and (E)-4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridine (0.68 g, 3.67 mmol) was added and the mixture stirred at room temperature, under nitrogen, overnight (20 hours). The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (2×50 ml). The extracts were washed with saturated brine (50 ml), combined and dried (magnesium sulfate). The residue after evaporation of the solvent was purified by flash chromatography, eluting with 20% then 25% ethyl acetate/petrol (60°-80°), to afford the title compound (0.4734 g, 49%). Recrystallisation from ethyl acetate/petrol (60°-80°) gave pale yellow needles, m.p. 122°-123° C.; (Found: C, 8.29; H, 6.58; N, 4.36. C22H21NO.0.1H2O requires C, 83.30; H, 6.74; N, 4.42%); δH (CDCl3) 2.43 (2H, br s, tetrahydropyridinyl CH2), 2.73 (2H, t, J 5.7Hz, tetrahydropyridinyl CH2), 3.21 (2H, d, J 2.7Hz, tetrahydropyridinyl CH2), 3.76 (2H, s, ArCH2N), 5.82 (1H, br s, tetrahydropyridinyl CH), 6.44 (1H, d, J 16.1Hz, CH=CHPh), 6.79 (1H, d, J 16.1Hz, CH=CHPh), 7.17-7.32 (5H, m, ArH), 7.39 (2H, m, ArH), 7.48 (1H, m, ArH), 7.58 (1H, s, 2-H), 7.73 (1H, m, ArH); m/z (ES+) 316 (M+1)+.

후처리

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in anhydrous dimethylformamide (10 ml)
  3. stirringthe mixture stirred at room temperature, under nitrogen, overnight (20 hours)
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe extracts were washed with saturated brine (50 ml)
  6. dry with materialdried (magnesium sulfate)
  7. customThe residue after evaporation of the solvent
  8. customwas purified by flash chromatography
  9. washeluting with 20%

출처 및 근거

ORD 기록
ord-1257316ad8234f0db436a880080a8841
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05681836

반응 노트

불러오는 중…