Sodium Hydroxide → HCID 19600057, compound

HRID 611059Notes

Reaction equation

HRID 611059 reaction equation
[CH2:1]([N:4]([CH2:11][CH2:12]Cl)[CH2:5][C:6]1[CH:10]=[CH:9][O:8][CH:7]=1)[CH:2]=[CH2:3].CCCCCC.C([Li])CCC.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:4]1[CH2:11][CH2:12][C:7]2[O:8][CH:9]=[CH:10][C:6]=2[CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19600271HCID 19600271, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 19600057HCID 19600057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9.03 g of the above crude N-allyl-N-(3-furylmethyl)-2-chloroethylamine in 200 ml of tetrahydrofuran, 63.8 ml (102 mmol) of 1.6 M n-butyl lithium hexane was added under ice-cooling, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. 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=9/1) to yield 5-allyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-9f7bcfd23951428fbec45f4b8ca11917
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

Loading…