Trifluoroacetic acid → 1-Propyne, 3-(1-ethoxyethoxy)-

HRID 1651361Notes

Reaction equation

HRID 1651361 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[CH:5]([O:7][CH2:8][CH3:9])=[CH2:6].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:5]([O:7][CH:8]([O:4][CH2:1][C:2]#[CH:3])[CH3:9])[CH3:6]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7859Propargyl alcoholHCID 8023Ethyl vinyl etherHCID 10340Sodium Carbonate

Product 1

HCID 867741-Propyne, 3-(1-ethoxyethoxy)-

Procedure

A solution of 20 g (0.36 mol) of 2-propyn-1-ol in 637 ml (6.66 mol) of ethyl vinyl ether was treated at 0° under argon with 1.27 ml (16.7 mmol) of trifluoroacetic acid and the mixture was subsequently stirred at room temperature for 65 hours. 1.3 g of sodium carbonate were added, the reaction mixture was stirred at room temperature for a further 30 minutes and concentrated on a rotary evaporator. Distillation of the residue under reduced pressure yielded 1-(1-ethoxyethoxy)-2-propyne of boiling point 55°/30 mmHg.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for a further 30 minutes
  2. concentrationconcentrated on a rotary evaporator
  3. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-0cf966651eef424a9bd669db8f37fd21
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

Loading…