Carbon Dioxide → HCID 19600120, compound

HRID 611241Notes

Reaction equation

HRID 611241 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[CH:14]=[CH:15][O:16][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([Li])CCC.[C:22](=[O:24])=[O:23]>O1CCCC1.CCCCCC>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[CH:14]=[C:15]([C:22]([O:24][CH3:17])=[O:23])[O:16][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 19600111HCID 19600111, compoundHCID 178418339Butyllithium

Product 1

HCID 19600120HCID 19600120, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 0.683 g (3.202 mmol) of 6-benzyl-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 30 ml of tetrahydrofuran, 4.0 ml (6.4 mmol) of 1.6 M n-butyl lithium in hexane was added under ice-cooling, followed by stirring for 0.5 hours. After the reaction mixture was cooled to -78° C., crushed dry ice was added; while the mixture was stirred vigorously, the mixture was allowed to warm to room temperature. After the solvent was distilled off under reduced pressure, the residue was dissolved in 50 ml of about 10% hydrogen chloride in methanol, followed by overnight stirring at room temperature. After the solvent was distilled off under reduced pressure, aqueous sodium hydrogen carbonate was added, followed by 3 extractions with dichloromethane. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1) to yield the desired product.

Workup

  1. temperaturecooling
  2. additionwas added
  3. stirringwhile the mixture was stirred vigorously
  4. temperatureto warm to room temperature
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. dissolutionthe residue was dissolved in 50 ml of about 10% hydrogen chloride in methanol
  7. waitfollowed by overnight
  8. stirringstirring at room temperature
  9. distillationAfter the solvent was distilled off under reduced pressure, aqueous sodium hydrogen carbonate
  10. additionwas added
  11. extractionfollowed by 3 extractions with dichloromethane
  12. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  13. distillationthe solvent was distilled off under reduced pressure
  14. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1)

Sources & evidence

ORD record
ord-fb5fcf785ca94715b162a0a3bfb2f1c8
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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