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

HRID 1651779Notes

Reaction equation

HRID 1651779 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 1n 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 subsequently stirred at room temperature for 65 hours. 1.3 g of sodium carbonate were added, the react ion 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. MS: 127 (M-H) m/e.

Workup

  1. stirringthe react ion 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-ec63efba3fea45e1bdae26c6eefae67c
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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