Water → 1-ethyl-5-(4-methoxyphenoxy)-3-methyl-1H-pyrazol-4-yl-phenyl-methanol

HRID 47622Notes

Reaction equation

HRID 47622 reaction equation
[CH2:1]([N:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[C:6]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[C:5]([CH3:25])=[N:4]1)[CH3:2].[BH4-].[Na+].O>CO>[CH2:1]([N:3]1[C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[C:6]([CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[OH:18])[C:5]([CH3:25])=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22747462[1-ethyl-5-(4-methoxyphenoxy)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

Product 1

HCID 227474811-ethyl-5-(4-methoxyphenoxy)-3-methyl-1H-pyrazol-4-yl-phenyl-methanolYield 69.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 77 mg of [1-ethyl-5-(4-methoxyphenoxy)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone and 119 mg of sodium borohydride in 5 ml of methanol was stirred at room temperature for 24 h. 20 ml of water was added and the mixture was extracted three times with 15 ml of diethyl ether. The combined extracts were dried over magnesium sulphate, filtered and evaporated to give 54 mg of [1-ethyl-5-(4-methoxyphenoxy)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanol as a colourless gum which was used without further purification. Mass spectrum (ES) m/z 339 [M+H]+, 380 [M+H+CH3CN]+.

Workup

  1. extractionthe mixture was extracted three times with 15 ml of diethyl ether
  2. dry with materialThe combined extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-31caa6fff1e549ff91bd5ed4d804dbeb
Source dataset
uspto-grants-2004_03
Patent number
US06699887B2

Reaction notes

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