Sodium hydride → HCID 15390573, 화합물

HRID 1418708노트

반응식

HRID 1418708 반응식
[H-].[Na+].[N:3]1([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[N:4]1.C1(C)C=CC(S(O[CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)(=O)=O)=CC=1>CN(C)C=O>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[O:28][CH2:27][CH2:26][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 1334121-(4-Hydroxybenzyl)pyrazoleHCID 14480093HCID 14480093, 화합물

생성물 1

HCID 15390573HCID 15390573, 화합물수율 40.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a mixture of 10 ml of anhydrous N,N-dimethylformamide and 72 mg of sodium hydride (60% oil dispersion) was added dropwise an anhydrous N,N-dimethyl-formamide (5 ml) solution of 300 mg of 4-(1-pyrazolyl)methylphenol under stirring over 10 minutes. After stirring at room temperature for 1 hour, the mixture was cooled to 5° to 10° C., to which an anhydrous N,N-dimethylformamide (5 ml) solution of 505 mg of 2-(2-pyridyloxy)ethyl p-toluenesulfonate was added dropwise over 30 minutes. The mixture was stirred at room temperature overnight and then at 60° to 70° C. for further 2 hours. The reaction mixture was poured into 50 ml of ice water, which was extracted twice with 30 ml of ethyl acetate. The organic layers were combined, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 208 mg of 4-(1-pyrazolyl)methylphenyl 2-(2-pyridyloxy)ethyl ether (compound 1). Yield, 41%.

후처리

  1. stirringAfter stirring at room temperature for 1 hour
  2. additionwas added dropwise over 30 minutes
  3. stirringThe mixture was stirred at room temperature overnight
  4. waitat 60° to 70° C. for further 2 hours
  5. extractionwas extracted twice with 30 ml of ethyl acetate
  6. washwashed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3f8b5d72802b41feb5e8734b44eb6f9c
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05883262

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