HCID 58197305, compound → HCID 15120644, compound

HRID 926457Notes

Reaction equation

HRID 926457 reaction equation
CC1(C)[O:7][C:6](=[O:8])[CH:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[C:4](=[O:20])[O:3]1>C(O)(C(F)(F)F)=O.O>[F:17][C:16]([F:18])([F:19])[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH:5]([C:6]([OH:8])=[O:7])[C:4]([OH:20])=[O:3])=[CH:11][CH:12]=1

Participants

3

Reactant 1

HCID 58197305HCID 58197305, compound

Product 1

HCID 15120644HCID 15120644, compound

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

To a 2 L flask containing 2,2-dimethyl-5-(4-(trifluoromethyl)benzyl)-1,3-dioxane-4,6-dione (65 g, 215 mmol, Intermediate 12: step a) was added a TFA/water solution (v/v, 560 mL/280 mL) at room temperature and the white suspension was heated between 70° C. and 78° C. in a large oil bath. The suspension did not dissolve until a temperature of 72° C. was reached. After approximately 40 minutes, the suspension became a clear homogeneous solution. After 3 hours, HPLC indicated that the reaction was complete. The mixture was concentrated on the rotary evaporator and azeotroped with toluene (4×100 mL) to give white solid which was used without further purification.

Workup

  1. temperaturethe white suspension was heated between 70° C. and 78° C. in a large oil bath
  2. dissolutionThe suspension did not dissolve until a temperature of 72° C.
  3. waitAfter 3 hours
  4. concentrationThe mixture was concentrated on the rotary evaporator
  5. customazeotroped with toluene (4×100 mL)
  6. customto give white solid which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-fbb8508c45b3475eae8a6b6e09896e3c
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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