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

HRID 1721681ノート

反応式

HRID 1721681 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-08d978ea2ec84eddb255d6f6dd0d4854
出典データセット
uspto-grants-1996_04
特許番号
US05512581

反応ノート

読み込み中…