Carbon Dioxide → HCID 21105508, compound

HRID 2099332Notes

Reaction equation

HRID 2099332 reaction equation
C([Li])CCC.Br[C:7]1[CH:20]=[CH:19][C:10]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1.[C:21](=[O:23])=[O:22]>C1COCC1.O>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][CH2:11][C:10]1[CH:19]=[CH:20][C:7]([C:21]([OH:23])=[O:22])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 247991602-((4-Bromobenzyl)oxy)pyridineHCID 178418339Butyllithium

Product 1

HCID 21105508HCID 21105508, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (1.6 M in hexane; 11.4 ml) was added to a solution of 2-(4-bromobenzyloxy)pyridine (4.2 g) in THF (120 ml) at −78° C. After 15 minutes, dry ice (7 g) was added. After warming to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The aqueous phase was acidified and again extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated. The product with the molecular weight of 229.24 (C13H11NO3); MS (ESI): 230 (M+H+) was obtained in this way.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionagain extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customMS (ESI): 230 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-078217c848da40f7809c14302bf8dfcc
Source dataset
uspto-grants-2009_08
Patent number
US07569583B2

Reaction notes

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