Potassium Carbonate → HCID 68982944, compound

HRID 353050Notes

Reaction equation

HRID 353050 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 (33.0 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-473957cfccfa44dd9f0d4a55901f5b07
Source dataset
uspto-grants-2004_06
Patent number
US06750214B2

Reaction notes

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