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

HRID 350888노트

반응식

HRID 350888 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-174fd5b4a5ff4b44bf32f1a9d5b9f5e1
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183296B2

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