Ethyl vinyl ether → 3-(1-Ethoxyethoxy)but-1-yne

HRID 2285667Notes

Reaction equation

HRID 2285667 reaction equation
[CH3:1][CH:2]([OH:5])[C:3]#[CH:4].[CH2:6]([O:8][CH:9]=[CH2:10])[CH3:7].OS([O-])(=O)=O.[K+]>C([O-])([O-])=O.[Na+].[Na+]>[CH3:7][CH:6]([O:5][CH:2]([C:3]#[CH:4])[CH3:1])[O:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 162393-Butyn-2-olHCID 516920Potassium bisulfate

Product 1

HCID 100120033-(1-Ethoxyethoxy)but-1-yneYield 91%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateCatalyst

Procedure

A mixture of 200 g of but-3-yn-2-ol and 240 g of ethylvinyl ether was added dropwise, at 30° and under nitrogen atmosphere, to 2 g of previously dried KHSO4. After stirring for 2 hours at 30° the reaction mixture was neutralized with 10 g of Na2CO3, then filtered, the organic phase being finally distilled on a VIGREUX column to give 369 g (91% yield) of 2-(3-oxa-pent-2-yloxy)-but-3-yne having b.p. 31°/16 Torr.

Workup

  1. filtrationfiltered
  2. distillationthe organic phase being finally distilled on a VIGREUX column

Sources & evidence

ORD record
ord-36969c47ca594b8095287b1d5bfffff0
Source dataset
uspto-grants-1982_04
Patent number
US04324729

Reaction notes

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