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

HRID 1377460Notes

Reaction equation

HRID 1377460 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

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 acetateetrol (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 5.7 Hz, tetrahydropyridinyl CH2), 3.21 (2H, d, J 2.7 Hz, tetrahydropyridinyl CH2), 3.76 (2H, s, ArCH2N), 5.82 (1H, br s, tetrahydropyridinyl CH), 6.44 (1H, d, J 16.1 Hz, C H=CHPh), 6.79 (1H, d, J 16.1 Hz, CH=C HPh), 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 (ES+) 316 (M+1)+.

Workup

  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%

Sources & evidence

ORD record
ord-727bf319a3a54418890b88cce0ff5adf
Source dataset
uspto-grants-1997_09
Patent number
US05665722

Reaction notes

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