Hydrochloric Acid → HCID 58942457, compound

HRID 17753Notes

Reaction equation

HRID 17753 reaction equation
Cl.[CH2:2]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23](=[O:26])[CH2:24][CH3:25])=[C:19]([O:27]COC)[C:18]=3[F:31])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)[CH2:3][CH3:4].O>C(O)C>[CH2:2]([CH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23](=[O:26])[CH2:24][CH3:25])=[C:19]([OH:27])[C:18]=3[F:31])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1)[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 589425491-(4-(4-(4-Propylcyclohexyl)phenyl)-3-fluoro-2-methoxymethoxyphenyl)-1-propanone

Product 1

HCID 58942457HCID 58942457, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17.7 mL of 1N hydrochloric acid was added to Compound (7) dissolved in 17.7 mL of ethanol, followed by refluxing under heating for 2 hours. After cooling the reaction solution to ambient temperature, water was added to the solution. The aqueous layer was extracted with toluene, which was added to the organic layer, and the organic layer was washed with a saturated salt solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel chromatography and recrystallization to obtain 1.48 g of 1-(4-(4-(4-propylcyclohexyl)phenyl)-3-fluoro-2-hydroxyphenyl)-1-propanone (Compound (1-2-2-21)) as colorless crystals.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 2 hours
  3. extractionThe aqueous layer was extracted with toluene, which
  4. additionwas added to the organic layer
  5. washthe organic layer was washed with a saturated salt solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by silica gel chromatography and recrystallization

Sources & evidence

ORD record
ord-f2fa54f0504f43e49c4bb3af8257153a
Source dataset
uspto-grants-2010_06
Patent number
US07740769B2

Reaction notes

Loading…