Water → HCID 21274676, compound

HRID 1382483Notes

Reaction equation

HRID 1382483 reaction equation
[NH:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1.C([O-])(O)=O.[Na+].O.Cl[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14]>C(O)C>[CH2:16]([O:15][C:13]([N:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1)=[O:14])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 962WaterHCID 18052Allyl chloroformateHCID 660593-PyrrolineHCID 516892Sodium Bicarbonate

Product 1

HCID 21274676HCID 21274676, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 3-pyrroline (3.5 gms) in ethanol (20 mL) was added ~25 mL saturated aq. NaHCO3 and enough water to allow rapid stirring. The mixture was cooled to 10° C. and allyl chloroformate (5.92 mL) was slowly added via pressure equalized addition funnel. The mixture was removed from ice bath and allowed to stir at room temperature for 2 hours. Product was extracted into Et2O (3×150 mL). The organic phase was washed with water (2×50 mL), dried (MgSO4) and solvent was evaporated at reduced pressure. Purification on silica (Et2O) afforded pure title compound.

Workup

  1. additionaddition funnel
  2. customThe mixture was removed from ice bath
  3. extractionProduct was extracted into Et2O (3×150 mL)
  4. washThe organic phase was washed with water (2×50 mL)
  5. dry with materialdried (MgSO4) and solvent
  6. customwas evaporated at reduced pressure
  7. customPurification on silica (Et2O)

Sources & evidence

ORD record
ord-4878e354115a4f0697e4898c06e66de4
Source dataset
uspto-grants-1989_02
Patent number
US04806637

Reaction notes

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