Ethyl bromoacetate → Ethyl 3-(2-ethoxy-2-oxoethoxy)picolinate

HRID 1804631Notes

Reaction equation

HRID 1804631 reaction equation
[OH:1][C:2]1[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O>[CH2:11]([O:10][C:8]([C:3]1[C:2]([O:1][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 15080989Ethyl 3-hydroxypicolinate

Product 1

HCID 21793317Ethyl 3-(2-ethoxy-2-oxoethoxy)picolinateYield 82.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2.0 g (12 mmol) of the title compound from Step A in 50 mL of acetone under an atmosphere of nitrogen was added 2.5 g (18 mmol) of potassium carbonate and 2.4 g (14 mmol) of ethyl bromoacetate. The reaction mixture was refluxed overnight. After cooling, the inorganic materials were filtered off and washed with acetone. The filtration was concentrated and purified by MPLC (Biotage Horizone: Flash 65i) eluent: 100% dichloromethane to 12% methanol in dichloromethane to give 2.5 g of the title compound as an oil. LC/MS: (M+1) 240.9

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe inorganic materials were filtered off
  4. washwashed with acetone
  5. filtrationThe filtration
  6. concentrationwas concentrated
  7. custompurified by MPLC (Biotage Horizone: Flash 65i) eluent

Sources & evidence

ORD record
ord-d2be60c67c4f4a22af624f96a821b912
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

Loading…