Water → 2-Cyclopentyl-2-(4-(2-quinolylmethoxy)phenyl)acetic acid methyl ester

HRID 1721681노트

반응식

HRID 1721681 반응식
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:7][CH:6]=1.[H-].[Na+].[CH:26]1(Br)[CH2:30][CH2:29][CH2:28][CH2:27]1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:23])[CH:4]([CH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:9][CH:10]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 14500224Methyl p-(2-quinolylmethoxy)phenylacetate

생성물 1

HCID 146748352-Cyclopentyl-2-(4-(2-quinolylmethoxy)phenyl)acetic acid methyl ester수율 70.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 4-(2-quinolylmethoxy)phenylacetic acid methyl ester (6.36 g; 20.7 mmol) in DMF (10 ml) at 0° C. was added in portions sodium hydride (60% dispersion in mineral oil) (840 mg; 21 mmol). The mixture was stirred at room temperature for 1 hour. It was then recooled to 0° C. and cyclopentyl bromide (2.38 ml, 22.0 mmol) was added dropwise. The resulting mixture was stirred at room temperature for 18 hours, and was then poured into water (50 ml). The product was extracted with ethyl acetate and purified by silica gel chromatography (hexane-ethyl acetate 3:1) to provide 5.5 g of 2-cyclopentyl-2-(4-(2-quinolylmethoxy)phenyl)acetic acid methyl ester.

후처리

  1. customwas then recooled to 0° C.
  2. stirringThe resulting mixture was stirred at room temperature for 18 hours
  3. extractionThe product was extracted with ethyl acetate
  4. custompurified by silica gel chromatography (hexane-ethyl acetate 3:1)

출처 및 근거

ORD 기록
ord-08d978ea2ec84eddb255d6f6dd0d4854
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05512581

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