Trifluoroacetic acid → 3,5-Diacetoxymethylpyrazole

HRID 236729Notes

Reaction equation

HRID 236729 reaction equation
C(C(O)=O)(F)(F)F.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:15]2[C:19]([CH2:20][O:21][C:22](=[O:24])[CH3:23])=[CH:18][C:17]([CH2:25][O:26][C:27](=[O:29])[CH3:28])=[N:16]2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>O>[C:27]([O:26][CH2:25][C:17]1[CH:18]=[C:19]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[NH:15][N:16]=1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 123775331-Triphenylmethyl-3,5-diacetoxymethylpyrazole

Product 1

HCID 123775343,5-Diacetoxymethylpyrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 90 ml. of CF3CO2H and 15 ml. of H2O, cooled to -20° was added, in portions, 10 g. (0.022 mol) of the end product of Example 20. After the addition was complete, the solution was stirred at -15° to -20° for 1 hour, poured into excess saturated K2CO3 solution and extracted with EtOAc. The organic phase was dried (MgSO4), concentrated and the residue chromatographed on silica gel to give the end product as a pale yellow oil. The analytical sample was obtained as a colorless oil by bulb to bulb distillation: bp 175 (0.05 mm).

Workup

  1. additionwas added, in portions, 10 g
  2. additionAfter the addition
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-ec3b0ec25d0f4d91a993dff32949e2d6
Source dataset
uspto-grants-1979_06
Patent number
US04157331

Reaction notes

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