Water → HCID 178422697, compound

HRID 2061109Notes

Reaction equation

HRID 2061109 reaction equation
[N:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[OH:8].C([O:11][C:12](=O)[CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1)[C:14](=O)[CH3:15])C.O>CO.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Zn+2]>[OH:7][C:6]1[N:1]=[C:2]2[O:8][C:12](=[O:11])[C:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)=[C:14]([CH3:15])[C:3]2=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10879985HCID 10879985, compoundHCID 178516109HCID 178516109, compound

Product 1

HCID 178422697HCID 178422697, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 104671Zinc trifluoromethanesulfonateCatalystHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

Zn(OTf)2 (669 mg, 1.84 mmol) was added to a suspension of pyridine-2,6-diol (204 mg, 1.84 mmol) and 2-(3-nitrobenzyl)-3-oxobutyric acid ethyl ester (488 mg, 1.84 mmol) in methanol (10 mL), and the mixture was stirred at 75° C. for 30 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate. It was then concentrated under reduced pressure to yield a crude product, which was then purified by column chromatography to yield the title compound (330 mg, 57%).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationIt was then concentrated under reduced pressure
  6. customto yield a crude product, which
  7. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-17b27ef82b704165bd1297f7a2699207
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

Loading…