Carbon Dioxide → HCID 25019181, compound

HRID 2043100Notes

Reaction equation

HRID 2043100 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].Br[C:7]1[CH:20]=[CH:19][C:10]([CH2:11][O:12]C2C=CC=CN=2)=[CH:9][CH:8]=1.[C:21](=O)=[O:22].C1C[O:27]CC1>O>[CH:4]1([CH2:21][O:22][C:7]2[CH:8]=[CH:9][C:10]([C:11]([OH:12])=[O:27])=[CH:19][CH:20]=2)[CH2:3][CH2:2][CH2:1]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 247991602-((4-Bromobenzyl)oxy)pyridineHCID 178418339Butyllithium

Product 1

HCID 25019181HCID 25019181, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-dbe89613d1994f56b1f5bb1dd2e8f67f
Source dataset
uspto-grants-2013_11
Patent number
US08586609B2

Reaction notes

Loading…