Carbon Dioxide → HCID 21105508, compound

HRID 1174716Notes

Reaction equation

HRID 1174716 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-f204e0f21b7945a18587fb57bdc92dcd
Source dataset
uspto-grants-2010_11
Patent number
US07838547B2

Reaction notes

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