Ammonium Chloride → 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile

HRID 350015노트

반응식

HRID 350015 반응식
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+].[CH2:20]([N:27]1[CH:31]=[C:30]([CH:32]=O)[C:29]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>C(COC)OC.CO>[CH2:20]([N:27]1[CH:31]=[C:30]([CH2:32][C:10]#[N:11])[C:29]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 161915Tosylmethyl isocyanideHCID 229307681-benzyl-3-(benzyloxy)-1H-pyrazole-4-carbaldehydeHCID 23665647Potassium tert-butoxide

생성물 1

HCID 693145121-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile수율 86.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 80711,2-Dimethoxyethane용매3회

실험 절차

A solution of p-toluenesufonylmethylisocyanide (10.3 g) in dimethoxyethane (50 ml) was added to a mixture of potassium t-butoxide (11.2 g) and dimethoxyethane (50 ml) at −78° C., and the mixture was stirred for 5 minutes. A solution of 1-benzyl-3-benzyloxy-1H-pyrazole-4-carbaldehyde (14.6 g) in dimethoxyethane (50 ml) was added to the mixture. After stirring at the same temperature for 1 hour, the mixture was stirred for 1 hour while raising the temperature. Methanol (150 ml) was added to the mixture, which was refluxed for 1 hour. After cooling, the reaction solution was poured into saturated aqueous ammonium chloride solution, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile (13.1 g, yield 86%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

후처리

  1. stirringAfter stirring at the same temperature for 1 hour
  2. stirringthe mixture was stirred for 1 hour
  3. temperaturewhile raising the temperature
  4. temperaturewas refluxed for 1 hour
  5. temperatureAfter cooling
  6. extractionwas extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-65956e39d6714037a78b49badad82e15
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

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