Trifluoroacetic acid → 2-(6-Methoxy-naphthalen-2-yl)-3-pentyl-benzofuran

HRID 1359248Notes

Reaction equation

HRID 1359248 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:27]=[CH:26][CH:25]=[CH:24][C:16]=3[C:17]=1[CH:18](O)[CH2:19][CH2:20][CH2:21][CH3:22])[CH:7]=[CH:6]2.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:27]=[CH:26][CH:25]=[CH:24][C:16]=3[C:17]=1[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 181827861-[2-(6-Methoxy-naphthalen-2-yl)-benzofuran-3-yl]-pentan-1-ol

Product 1

HCID 181827882-(6-Methoxy-naphthalen-2-yl)-3-pentyl-benzofuranYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 1-[2-(6-methoxy-naphthalen-2-yl)-benzofuran-3-yl]-pentan-1-ol (15.5 g, 43 mmol) and triethyl silane (10 g, 86 mmol) in methylene chloride (300 mL) was cooled in an ice bath. Trifluoro acetic acid (50 mL) was added gradually. The mixture was stirred at while cooling for 2 hours then was allowed to warm to room temperature. The solvent was evaporated. The residue was dissolved in ether and washed with sodium bicarbonate solution, then with water. The solvent was evaporated and the residue was purified by flash chromatography on silica gel using 4% ethyl acetate in hexane as the mobile phase. The product was obtained as a clear oil (8.9 g). 1HNMR (300 MHz, DMSO-d6): δ8.22 (s, 1H), 7.98-7.92 (m, 2H), 7.95-7.90 (m, 2H), 7.64 (d, 1H, J=8.8 Hz), 7.65 (d, 1H, J=8.8 Hz), 7.58 (d, 1H, J=8.8 Hz), 7.38-7.20 (m, 4H), 3.90 (s, 3H), 2.96 (t, 1H, J =9.9 Hz), 1.70 (p, 1H, J=7.0 Hz), 1.42-1.26 (m, 4H), and 0.82 ppm (t, 3H, J=7.4 Hz).

Workup

  1. temperaturewhile cooling for 2 hours
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with sodium bicarbonate solution
  5. customThe solvent was evaporated
  6. customthe residue was purified by flash chromatography on silica gel using 4% ethyl acetate in hexane as the mobile phase

Sources & evidence

ORD record
ord-6654e753c7524b09a4c722d9451e573b
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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