Trifluoroacetic acid → HCID 69199322, compound

HRID 898350Notes

Reaction equation

HRID 898350 reaction equation
C([SiH](CC)CC)C.[CH2:8]([C:10]1[O:11][C:12]2[CH:26]=[CH:25][CH:24]=[CH:23][C:13]=2[C:14]=1[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)O)[CH3:9].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:15]([C:14]1[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[O:11][C:10]=1[CH2:8][CH3:9])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 15307873HCID 15307873, compound

Product 1

HCID 69199322HCID 69199322, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylsilane (18.46 g; 0.159 mol) was added slowly to the solution of (2-ethyl-benzofuran-3-yl)-phenyl-methanol (20 g; 0.079 mol) in methylene chloride (200 mL) while stirring and cooling in ice bath under an atmosphere of nitrogen. Trifluoroacetic acid (40 mL) was then added dropwise. The mixture was then stirred at room temperature for one hour and the solvent was then evaporated. The residue was extracted with ether and the ethereal extracts were combined, washed with sodium bicarbonate solution, water, dried over anhydrous magnesium sulfate and the solvent was evaporated to give the product (19.2 g) as an oil. Mass spectrum (ESI, [M+] m/z 236. 1HNMR (400 MHz, DMSO-d6): δ 1.22 (t, 3H, J=7.47 Hz), 2.91 (q, 2H, J=7.47 Hz), 3.97 (s, 2H), 7.08 (dt, 1H, J=7.25, 1.1 Hz), 7.12-7.2 (m, 2H), 7.24-7.26 (m, 4H). 7.34-7.37 (m, 1H), 7.43-7.46 (m, 1H). Elemental Analysis for C17H16O: Calculated: C, 86.41; H, 6.82. Found: C, 86.16; H, 6.71.

Workup

  1. temperaturecooling in ice bath under an atmosphere of nitrogen
  2. stirringThe mixture was then stirred at room temperature for one hour
  3. customthe solvent was then evaporated
  4. extractionThe residue was extracted with ether
  5. washwashed with sodium bicarbonate solution, water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-123c434ab5d644e89a0648e595a7cf3e
Source dataset
uspto-grants-2008_04
Patent number
US07351726B2

Reaction notes

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