Toluene → HCID 69714704, compound

HRID 495346Notes

Reaction equation

HRID 495346 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.C([O-])(O)=O.[Na+].[C:16]1(C)C=CC=C[CH:17]=1>FC(F)(F)C(O)=O.CC(OC)(C)C>[CH2:8]([CH:9]1[CH2:10][CH2:5][CH:3]=[CH:2][O:1]1)[CH2:7][CH:6]=[CH:16][CH3:17]

Participants

6

Reactant 3

HCID 1140TolueneHCID 68490alpha-HydroxyacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 69714704HCID 69714704, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
50 °C

Procedure

The cyclic vinyl ether (2 eq.) was added to a suspension of the hydroxy-acetophenone (10 mmol) in toluene (10 ml), followed by trifluoroacetic acid (2 or 3 drops, ˜0.01 eq.). The mixture was heated at 50° C. When the reaction was complete (TLC, 2-3 hours), it was diluted with MTBE and poured into aq. NaHCO3 (sat.). The aqueous phase was separated and extracted with MTBE, and the combined organic layers were washed with brine and dried over MgSO4. The crude, obtained after evaporation of the solvents, was purified by chromatography (SiO2, EtOAc/Hexane) to afford the desired product as a colorless to pale yellow oil.

Workup

  1. custom(TLC, 2-3 hours), it
  2. customThe aqueous phase was separated
  3. extractionextracted with MTBE
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customThe crude, obtained
  7. customafter evaporation of the solvents
  8. customwas purified by chromatography (SiO2, EtOAc/Hexane)

Sources & evidence

ORD record
ord-a4b7d0094ef0486aad111d5bca936574
Source dataset
uspto-grants-2005_09
Patent number
US06939845B2

Reaction notes

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