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

HRID 1490039ノート

反応式

HRID 1490039 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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)+.

後処理

  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%

出典と根拠

ORDレコード
ord-1257316ad8234f0db436a880080a8841
出典データセット
uspto-grants-1997_10
特許番号
US05681836

反応ノート

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