Propyne → HCID 21529911, compound

HRID 1658006Notes

Reaction equation

HRID 1658006 reaction equation
[N:1]([CH2:4][C:5]([OH:7])=[O:6])=[N+:2]=[N-:3].B(F)(F)F.CCOCC.[CH:17]#[C:18][CH3:19]>C(Cl)Cl>[N:1]([CH2:4][C:5]([O:7][C:18]([CH3:19])=[CH2:17])=[O:6])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 6335PropyneHCID 8000Boron trifluoride etherateHCID 155605Azidoacetic acid

Product 1

HCID 21529911HCID 21529911, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Azidoacetic acid (5.35 g, 0.05 mole) and mercuric acetate (1.82 g, 5.7 mMoles) are added to 50 ml of methylene chloride containing 0.1 ml of boron trifluoride etherate. Propyne, which had been passed through Linde Co. Molecular Sieves 4A, is bubbled slowly through the mixture for 3 hours. Sodium bicarbonate (0.5 g) is added and the mixture is filtered through a short Florisil column. The eluent is concentrated in vacuo and the residue obtained is purified by vacuum distillation to give isopropenyl azidoacetate.

Workup

  1. customMolecular Sieves 4A, is bubbled slowly through the mixture for 3 hours
  2. additionSodium bicarbonate (0.5 g) is added
  3. filtrationthe mixture is filtered through a short Florisil column
  4. concentrationThe eluent is concentrated in vacuo
  5. customthe residue obtained
  6. distillationis purified by vacuum distillation

Sources & evidence

ORD record
ord-395f5b6c36b84dbd9bb77d486ee9b9b9
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

Loading…