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

HRID 350879Notes

Reaction equation

HRID 350879 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-b3364769436b4434bea69814494f1ba9
Source dataset
uspto-grants-2007_02
Patent number
US07183296B2

Reaction notes

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