Hydrochloric Acid → HCID 23157462, compound

HRID 2110866Notes

Reaction equation

HRID 2110866 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][O:26]COC)=[CH:21][CH:20]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.CO>O>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][CH:20]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 23159900HCID 23159900, compound

Product 1

HCID 23157462HCID 23157462, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-tert-butyl-1-{4-[(methoxymethoxy)methyl]benzyl)-5-(phenoxymethyl)-1H-pyrazole (1.66 g, 4.21 mmol), concentrated hydrochloric acid (0.2 mL) and methanol (20 mL) was refluxed overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (1.35 g, yield 91%) as a colorless oil.

Workup

  1. temperaturewas refluxed overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract washed with aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04cf16d3fe984d3a9108f9997cc34e4a
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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