Trifluoroacetic acid → 3-(2-Cyclopentylethyl)-2-(6-methoxy-2-naphthyl)-1-benzofuran

HRID 1359214Notes

Reaction equation

HRID 1359214 reaction equation
[CH:1]1([CH2:6][CH:7]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]=2[C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH3:29])[CH:24]=3)[CH:19]=2)O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1([CH2:6][CH2:7][C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]=2[C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH3:29])[CH:24]=3)[CH:19]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 181828152-Cyclopentyl-1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-ethanol

Product 1

HCID 181827813-(2-Cyclopentylethyl)-2-(6-methoxy-2-naphthyl)-1-benzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-cyclopentyl-1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-ethanol (1.84 g, 4.77 mmol) in methylene chloride (50 mL) cooled in an ice bath was added triethylsilane (1.5 mL, 9.5 mmol). Trifluoroacetic acid (3.7 mL, 48 mmol) was then added drop-wise. The reaction mixture was stirred at room temperature for 1 hour, then concentrated. The residue was partitioned in ethyl acetate and sodium bicarbonate solution. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by flash chromatography (Biotage apparatus) using 100% hexane as an eluant afforded 3-(2-cyclopentylethyl)-2-(6-methoxy-2-naphthyl)-1-benzofuran as a light beige wax (1.05 g). 1HNMR (200 MHz, DMSO-d6): δ8.25 (s, 1H), 7.95 (d, 2H, J=7.7 Hz), 7.85 (d, 1H. J=7.7 Hz), 7.55-7.75 (m, 2H), 7.2-7.4 (m, 4H), 3.9 (s, 3H), 2.95-3.05 (m, 2H), 1.4-2.0 (br m, 9H), and 1.1-1.3 ppm (br m, 2H).

Workup

  1. temperaturecooled in an ice bath
  2. concentrationconcentrated
  3. customThe residue was partitioned in ethyl acetate
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record
ord-a189661c583a4b2cbb0e67cb534051a5
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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