Trifluoroacetic acid → HCID 18766516, compound

HRID 480702Notes

Reaction equation

HRID 480702 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH:21]=[CH:22][CH:23]=1)[O:10][C:11]([CH3:20])([CH3:19])[C:12]([O:14]C(C)(C)C)=[O:13])=[O:6])[CH:2]=[CH2:3].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH:21]=[CH:22][CH:23]=1)[O:10][C:11]([CH3:19])([CH3:20])[C:12]([OH:14])=[O:13])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18766572HCID 18766572, compound

Product 1

HCID 18766516HCID 18766516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-(3-allyloxycarbonylphenoxy)-2-methylpropionate (11.59 g, 36.19 mmol) was dissolved in dichloromethane (20 mL). Subsequently, trifluoroacetic acid (40 mL) was added at room temperature, and the mixture was stirred for three hours. The reaction mixture was concentrated under reduced pressure, and toluene was added to the concentrate. The resultant mixture was concentrated again under reduced pressure. Ethyl acetate was added. Washing was performed sequentially with water and saturated brine, followed by drying over sodium sulfate. The reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby a yellow oil was obtained (8.30 g, 31.41 mmol, 86.7%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and toluene
  2. additionwas added to the concentrate
  3. concentrationThe resultant mixture was concentrated again under reduced pressure
  4. additionEthyl acetate was added
  5. washWashing
  6. dry with materialby drying over sodium sulfate
  7. filtrationThe reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby a yellow oil
  8. customwas obtained (8.30 g, 31.41 mmol, 86.7%)

Sources & evidence

ORD record
ord-0436ca1050584440a42f903e3ab62bdf
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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