Pyridine → HCID 178447886, compound

HRID 1004535Notes

Reaction equation

HRID 1004535 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].N1C=CC=CC=1.C1(C)C=CC=CC=1.[CH2:27]([C@H:30]1[CH2:35][CH2:34][C@H:33]([C:36]2[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)[CH2:28][CH3:29]>O>[CH2:27]([C@H:30]1[CH2:31][CH2:32][C@H:33]([C:36]2[CH:44]=[CH:43][C:39]([C:40]([O:13][C:4]3[CH:5]=[CH:6][C:7]([O:8][C:9]([F:11])([F:12])[F:10])=[C:2]([F:1])[CH:3]=3)=[O:41])=[CH:38][CH:37]=2)[CH2:34][CH2:35]1)[CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140Toluene2×HCID 27833573-Fluoro-4-(trifluoromethoxy)phenolHCID 178447883HCID 178447883, compound

Product 1

HCID 178447886HCID 178447886, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, 1.3 g (6.5 mmol) of 3-fluoro-4-trifluoromethoxyphenol, 0.8 ml of pyridine, and 3 ml of toluene were mixed. To this mixture was added dropwise 3 ml of toluene solution containing 6.5 mmol of 4-(trans-4-propylcyclohexyl)benzoyl chloride at room temperature in 5 minutes. After the dropping was finished, they were reacted at 50° C. for 3 hours. After finishing of the reaction, 15 ml of water was added to the reaction product, and then extracted with 40 ml of toluene. The organic layer thus obtained was washed with 6N-hydrochloric acid thrice, 2N-sodium hydroxide thrice, and water thrice, and then dried over anhydrous magnesium sulfate. Solvent was distilled off at a reduced pressure and the residue was subjected to a silica gel column chromatography (eluent: toluene) to obtain 2.6 g of a crude 3-fluoro-4-trifluoromethoxyphenyl 4-(trans-4-propyl-cyclohexyl)benzoate. This product was recrystallized from a mixed solvent of heptane/ether (1/1) to obtain 2.4 g (yield: 85.6%) of the subject compound.

Workup

  1. customthey were reacted at 50° C. for 3 hours
  2. additionwas added to the reaction product
  3. extractionextracted with 40 ml of toluene
  4. customThe organic layer thus obtained
  5. washwas washed with 6N-hydrochloric acid thrice, 2N-sodium hydroxide thrice, and water thrice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationSolvent was distilled off at a reduced pressure

Sources & evidence

ORD record
ord-79dc29aea7da4e6bac2f508dd3df9ab8
Source dataset
uspto-grants-2000_04
Patent number
US06051288

Reaction notes

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