Water → 5-(3-Pyridylmethoxy)benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 648040노트

반응식

HRID 648040 반응식
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[S:11][C:10]2[CH:12]=[CH:13][C:14]([OH:16])=[CH:15][C:9]=2[CH:8]=1)=[O:6].Cl[CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.O>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[S:11][C:10]2[CH:12]=[CH:13][C:14]([O:16][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][C:9]=2[CH:8]=1)=[O:6]

참가 물질

6

반응물 4

HCID 962WaterHCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 13662999Methyl 5-hydroxybenzo[b]thiophene-2-carboxylate

생성물 1

HCID 544677875-(3-Pyridylmethoxy)benzo[b]thiophene-2-carboxylic acid methyl ester수율 53.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (0.24 g. of 50% dispersion in mineral oil) was added portionwise to a solution of 5-hydroxybenzo[b]thiophene-2-carboxylic acid methyl ester (1.04 g.) in dry N,N-dimethylformamide (10 ml.) and the mixture was stirred at room temperature for 30 minutes. 3-Chloromethylpyridine (0.65 g.) in dry N,N-dimethylformamide (5 ml.) was then added and the mixture was stirred at room temperature for 1 hour, and then poured into water. The mixture was extracted several times with ethyl acetate and the combined extracts were washed well with water and dried (Na2SO4). Evaporation of the solvent gave a solid which was washed with petrol and crystallized from isopropanol to give 5-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylic acid methyl ester (0.80 g.), m.p. 126°-127° C.

후처리

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionThe mixture was extracted several times with ethyl acetate
  3. washthe combined extracts were washed well with water
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent
  6. customgave a solid which
  7. washwas washed with petrol
  8. customcrystallized from isopropanol

출처 및 근거

ORD 기록
ord-0b26e4de84fb42a08b93153569c8f56a
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04410539

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