Water → 4-[4-(3-Chloro-propoxy)-phenyl]-4-oxo-2-pyridin-2-yl-butyric acid ethyl ester

HRID 2042637Notes

Reaction equation

HRID 2042637 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[H-].[Na+].Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][Cl:29])=[CH:21][CH:20]=1)=[O:18].O>CN(C)C=O>[CH2:11]([O:10][C:8](=[O:9])[CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][Cl:29])=[CH:21][CH:20]=1)=[O:18])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75960Ethyl 2-pyridylacetateHCID 140970932-Bromo-1-[4-(3-chloro-propoxy)-phenyl]-ethanone

Product 1

HCID 596520644-[4-(3-Chloro-propoxy)-phenyl]-4-oxo-2-pyridin-2-yl-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a 500 mL round bottom flask ethyl 2-pyridylacetate (2.0 g, 12.1 mmol), and 60% sodium hydride (508 mg, 12.7 mmol) in dimethylformamide (50 mL) was stirred 1 h. 2-Bromo-1-[4-(3-chloro-propoxy)-phenyl]-ethanone (3.53 g, 12.1 mmol) was then added in dimethylformamide (50 mL) via dropping funnel. The reaction was stirred 14 h. Water (300 mL) was added and the organics were extracted three times with ethyl acetate, and then dried over MgSO4. Purification with silica gel chromatography eluting with hexanes/ethyl acetate (3:1) produced 2.8 g (62%). MS m/z 376 (M+H).

Workup

  1. extractionthe organics were extracted three times with ethyl acetate
  2. dry with materialdried over MgSO4
  3. customPurification with silica gel chromatography
  4. washeluting with hexanes/ethyl acetate (3:1)
  5. customproduced 2.8 g (62%)

Sources & evidence

ORD record
ord-b046712e335048a29786ae3387708d67
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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