Trifluoroacetic acid → HCID 58415294, compound

HRID 2075207Notes

Reaction equation

HRID 2075207 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[S:13][CH:14]=[CH:15][N:16]=3)O)=[CH:9][C:4]=2[CH:3]=[CH:2]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl.CCOC(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:12]3[S:13][CH:14]=[CH:15][N:16]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58415351HCID 58415351, compound

Product 1

HCID 58415294HCID 58415294, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon at 24° C., crude benzofuran-5-yl(thiazol-2-yl)methanol (2.50 g, 10.8 mmol) was dissolved in 1,2-dichloroethane (40 mL), treated with triethylsilane (3.14 g, 27.0 mmol) and trifluoroacetic acid (1.25 mL, 16.2 mmol), and heated to reflux for 20 h. The mixture was diluted with EtOAc and ice, washed 1× with saturated aqueous NaHCO3, brine, dried over MgSO4, and evaporated. Purification by flash chromatography (hexanes to hexanes/EtOAc=3:2) gave 2-(benzofuran-5-ylmethyl)thiazole as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.71 (d, J=3.3 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.55 (br. s, 1H), 7.47 (d, J=8.4 Hz, 1H), 7.27-7.24 (m, 1H), 7.19 (d, J=3.3 Hz, 1H), 6.74-6.73 (m, 1H), 4.44 (s, 2H). MS (ESI) m/z: Calculated: 215.0; Observed: 216.1 (M++1).

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 h
  3. washwashed 1× with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customPurification by flash chromatography (hexanes to hexanes/EtOAc=3:2)

Sources & evidence

ORD record
ord-dee2155e0abc4dedbc0196d651a048ae
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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