Trifluoroacetic acid → HCID 68698368, compound

HRID 2234200Notes

Reaction equation

HRID 2234200 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][O:13][CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17].FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][O:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86258460HCID 86258460, compound

Product 1

HCID 68698368HCID 68698368, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-[2-(2-naphthyl)ethoxy]propanoate (Example 32a) (4.96 g) was dissolved in DCM (25 ml), and trifluoroacetic acid (25.5 ml) added. The mixture was stirred for 1 hour. The solvents were removed in vacuo, and the residue taken up in ether. The ether was washed with saturated bicarbonate solution (×3) and the aqueous layer was acidified with 2N HCl, then extracted with ether (×3), dried over magnesium sulfate, filtered and evaporated to give the sub-titled compound (3.66 g).

Workup

  1. customThe solvents were removed in vacuo
  2. washThe ether was washed with saturated bicarbonate solution (×3)
  3. extractionextracted with ether (×3)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-110bb6bbd3a14a7885650d4c0eda4997
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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