Trifluoroacetic acid → HCID 13356241, compound

HRID 1626844Notes

Reaction equation

HRID 1626844 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:9][CH:10]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[OH:4][C:5]1[CH:6]=[C:7]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57742132HCID 57742132, compound

Product 1

HCID 13356241HCID 13356241, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Ethyl 2-(3-(methoxymethoxy)phenyl)propanoate (4.17 g, 17.5 mmol) in CH2Cl2 (80 mL) was added trifluoroacetic acid (40 mL) at 0° C. The reaction mixture was stirred for 1 hrs at 0° C., and basified with NaHCO3 (60 g). The mixture was diluted with H2O (250 mL) slowly and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:4) as eluant.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-7b5eddb3077948a389e1ae4595ef2b2a
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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