Water → Methyl 2-(5-chloro-3-pyridyloxy)butyrate

HRID 1374888Notes

Reaction equation

HRID 1374888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:16]([CH2:21][CH3:22])[C:17]([O:19][CH3:20])=[O:18].O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:16]([CH2:21][CH3:22])[C:17]([O:19][CH3:20])=[O:18])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 95577Butanoic acid, 2-bromo-, methyl esterHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 21078438Methyl 2-(5-chloro-3-pyridyloxy)butyrate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5-Chloro-3-pyridinol (10.0 g) was dissolved in anhydrous N,N-dimethyl formamide (150 ml) containing anhydrous potassium carbonate (21.2 g) and methyl 2-bromobutyrate (16.4 ml). The mixture was stirred at 70° C. for 1.5 hours and allowed to cool to ambient temperature. The mixture was poured into water, extracted with diethyl ether (three times) and the combined extracts were washed with water (twice), dried over magnesium sulphate and evaporated under reduced pressure to give the required product as a pale brown oil, 27.4 g.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with diethyl ether (three times)
  3. washthe combined extracts were washed with water (twice),
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-779f341786384658a93497896fc77039
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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