Water → 5-(3,5-dichloro-phenylsulphanyl)-1-ethyl-3-methyl-1H-pyrazol-4-yl-methanol

HRID 350888

Reaction equation

HRID 350888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH3:16])[N:13]=[C:12]([CH3:17])[C:11]=2[CH:18]=[O:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH3:16])[N:13]=[C:12]([CH3:17])[C:11]=2[CH2:18][OH:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 227474955-(3,5-dichloro-phenylsulphanyl)-1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 227475205-(3,5-dichloro-phenylsulphanyl)-1-ethyl-3-methyl-1H-pyrazol-4-yl-methanolYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.1 g of 5-(3,5-dichloro-phenylsulphanyl)-1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde and 0.53 g of sodium borohydride in 25 ml of anhydrous methanol was stirred under nitrogen at room temperature for 15 minutes. Water (25 ml) was added and the mixture was extracted three times with 20 ml of diethyl ether. The combined extracts were dried over magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using ethyl acetate/petroleum ether (bp 40–60° C.) (1:3) for the elution to give 902 mg of 5-(3,5-dichloro-phenylsulphanyl)-1-ethyl-3-methyl-1H-pyrazol-4-yl-methanol as a yellow oil. Mass spectrum (ES) m/z 317 [M+H]+.

Workup

  1. extractionthe mixture was extracted three times with 20 ml of diethyl ether
  2. dry with materialThe combined extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-174fd5b4a5ff4b44bf32f1a9d5b9f5e1
Source dataset
uspto-grants-2007_02
Patent number
US07183296B2

Linked notes

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