Carbon Dioxide → (1-Butyl-2-oxo-1,2-dihydropyridin-4-yl)acetic acid

HRID 733339Notes

Reaction equation

HRID 733339 reaction equation
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7].[Li+].[CH3:9]C([N-]C(C)C)C.[C:16](=[O:18])=[O:17].Cl.[CH2:20]1[CH2:24]O[CH2:22][CH2:21]1>>[CH2:22]([N:1]1[CH:6]=[CH:5][C:4]([CH2:9][C:16]([OH:18])=[O:17])=[CH:3][C:2]1=[O:7])[CH2:21][CH2:20][CH3:24]

Participants

6

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 88712-PyridoneHCID 2724682Lithium diisopropylamide

Product 1

HCID 53429105(1-Butyl-2-oxo-1,2-dihydropyridin-4-yl)acetic acidYield 66%

Procedure

A solution of pyridinone ix (1.7 g, 10.3 mmol) in 20 mL anhydrous THF is added dropwise to a solution of LDA (2 M, 5.7 mL, 6.05 mmol) in 40 mL anhydrous THF at −78° C. The solution is allowed to stir for 45 minutes followed by the addition of solid CO2 (10 g). After 0.5 h the mixture is poured onto H2O and acidified with 1 N HCl. The solution is concentrated under reduced pressure and extracted with ethyl acetate and CH2Cl2. The combined organics are dried over MgSO4, filtered and concentrated to give a solid which is purified by flash chromatography (9/1:CH2Cl2/MeOH) to provide x as a white solid (1.4 g, 66%). (MS: M+H: 210.0).

Workup

  1. additionAfter 0.5 h the mixture is poured onto H2O
  2. concentrationThe solution is concentrated under reduced pressure
  3. extractionextracted with ethyl acetate and CH2Cl2
  4. dry with materialThe combined organics are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a solid which
  8. customis purified by flash chromatography (9/1:CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-dc9e87da64d34b028dde1b40045116c7
Source dataset
uspto-grants-2009_09
Patent number
US07589094B2

Reaction notes

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