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

HRID 1721681Notes

Reaction equation

HRID 1721681 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-08d978ea2ec84eddb255d6f6dd0d4854
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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