Hydrochloric Acid → HCID 21090736, compound

HRID 351264Notes

Reaction equation

HRID 351264 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:19]=[C:18]([C:29]([F:32])([F:31])[F:30])[C:17]=2[CH3:33])=[CH:12][CH:11]=1)(C)(C)C.Cl>CCO>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([N:20]2[C:16]([C:13]3[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][OH:6])=[CH:11][CH:12]=3)=[C:17]([CH3:33])[C:18]([C:29]([F:32])([F:31])[F:30])=[N:19]2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69331778HCID 69331778, compound

Product 1

HCID 21090736HCID 21090736, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[4-(2-{[tert-butyl(dimethyl)-silyl]oxy}ethoxy)phenyl]-1-(4-methoxyphenyl)-4-methyl-3-(trifluoromethyl)-1H-pyrazole (5.2 g) in EtOH (200 ml) was added conc.HCl (20 ml) at room temperature. After stirring for 2 hrs, the reaction mixture was partitioned between EtOAc and water. Organic layer was separated and washed with water, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (Hex/EtOAc=2:1–1:1) to give 2.05 g (51%) of 2-{4-[1-(4-methoxyphenyl)-4-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenoxy}ethanol as a crystal.

Workup

  1. customat room temperature
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. customOrganic layer was separated
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed on silica gel (Hex/EtOAc=2:1–1:1)

Sources & evidence

ORD record
ord-1fab55794c474593a255cbbc8b49ba0f
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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