Ethyl vinyl ether → 4-(1-Ethoxyethoxy)-1-butyne

HRID 1837080Notes

Reaction equation

HRID 1837080 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[CH:6]([O:8][CH2:9][CH3:10])=[CH2:7].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:6]([O:8][CH:9]([O:5][CH2:1][CH2:2][C:3]#[CH:4])[CH3:10])[CH3:7]

Participants

6

Reactant 3

HCID 8023Ethyl vinyl etherHCID 135663-Butyn-1-OLHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 131717324-(1-Ethoxyethoxy)-1-butyneYield 85.5%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

3-Butyn-1-ol (46.33 g, 0.661 mole) in methylene chloride (700 mL) was treated with ethyl vinyl ether (0.661 mole, 63.2 mL) and pyridinium p-toluenesulfonate (0.033, 8.31 g) (note: upon addition of pyridinium p-toluenesulfonate an exothermic reaction takes place). After stirring 2 hours, the reaction mixture was concentrated and filtered through a pad of silica gel (ethyl acetate:hexane, 1:1) to provide the title compound as a colorless liquid (80.29 g, 85.5%).

Workup

  1. customan exothermic reaction
  2. concentrationthe reaction mixture was concentrated
  3. filtrationfiltered through a pad of silica gel (ethyl acetate:hexane, 1:1)

Sources & evidence

ORD record
ord-b3d4ea71835d49ae9e5674d4030563cb
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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