Trifluoroacetic acid → HCID 13356241, compound

HRID 660322Notes

Reaction equation

HRID 660322 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13]COC)[CH:8]=1)[CH3:6])[CH3:2].C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

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

Product 1

HCID 13356241HCID 13356241, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(3-methoxymethoxy-phenyl)-propionic acid ethyl ester in the dichloromethane was added dropwise TFA (150 mL) at 0□. The reaction mixture was stirred 1 h at 0°, and solid sodium bicarbonate (200 g) was added very slowly. The resulting mixture was poured into ice water very slowly and extracted with EtOAc. The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1 to 4:1) to afford the product as colorless oil. (19.0 g, 70.4% 2 steps)

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1 to 4:1)

Sources & evidence

ORD record
ord-d29e75cba36e4ac481f9c5a3f5dbee53
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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