Potassium Carbonate → HCID 68982944, compound

HRID 1871490Notes

Reaction equation

HRID 1871490 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][C:8]([O:9][CH3:10])=[C:6]([OH:7])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].O([CH2:28][C:29]([F:32])([F:31])[F:30])S(C(F)(F)F)(=O)=O>CN(C=O)C.C(Cl)Cl>[CH3:10][O:9][C:8]1[CH:11]=[CH:12][C:4]([C:3]([O:2][CH3:1])=[O:13])=[CH:5][C:6]=1[O:7][CH2:28][C:29]([F:32])([F:31])[F:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 68982944HCID 68982944, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of isovanillic acid methyl ester (3.0 g, 0.18 mol) and potassium carbonate (41.4 g, 0.30 mol) in DMF (100 ml) was added a solution of trifluoroethyl triflate [Burdon et al Tetrahedron 21, 1 (1965)] (65.0 g, 0.28 mol) in CH2Cl2. The mixture was stirred at room temperature for 18 h then evaporated to 50 ml, the mixture partitioned between ether and H2O, the organic layer washed with H2O and saturated brine, then dried over MgSO4 and evaporated. The resulting solid was triturated with hexane to give the subtitle compound as an off-white solid (42.55 g, 90%). Rf 0.47 (CH2Cl2). MS m/z 265 (MH+).

Workup

  1. customthen evaporated to 50 ml
  2. customthe mixture partitioned between ether and H2O
  3. washthe organic layer washed with H2O and saturated brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe resulting solid was triturated with hexane

Sources & evidence

ORD record
ord-50a077a602eb4ca69b71f7400fd528a4
Source dataset
uspto-grants-2000_08
Patent number
US06103738

Reaction notes

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