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Bromocyclopentane → Methyl 5-(cyclopentyloxy)-6-methoxy-3-pyridinecarboxylate

HRID 1825394
Notes
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Reaction equation

HRID 1825394 reaction equation
[OH:1][C:2]1[C:3]([O:12][CH3:13])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH:20]1(Br)[CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C)C=O.O>[CH:20]1([O:1][C:2]2[C:3]([O:12][CH3:13])=[N:4][CH:5]=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:24][CH2:23][CH2:22][CH2:21]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 22145686Methyl 5-hydroxy-6-methoxynicotinate

Product 1

HCID 22145812Methyl 5-(cyclopentyloxy)-6-methoxy-3-pyridinecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 5-hydroxy-6-methoxynicotinoate (250 mg), anhydrous potassium carbonate (600 mg) and cyclopentyl bromide (0.26 mL) in dry dimethylformamide (5 mL) is stirred and heated at 60±5° C. for 24 hours. The mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The extracts are washed with water and dried (MgSO4). Concentration gave methyl 5-cyclopentyloxy-6-methoxynicotinoate (290 mg) as an oil.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extracts are washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration

Sources & evidence

ORD record
ord-af368b2bd62242aba43021fa0d97d70b
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07045660B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes