{{Chembox | ImageFile = Ethyl vinylether.svg | ImageSize = | ImageAlt = | PIN = Ethoxyethene | OtherNames = Ethoxyethylene, ''Vinamar'' |Section1={{Chembox Identifiers | CASNo = 109-92-2 | ChemSpiderID = 7732 | PubChem = 8023 | EC_number = 203-718-4 | RTECS = KO0710000 | UNNumber = 1302 | UNII = 6235C9592H | ChEMBL = 116745 | StdInChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3 | StdInChIKey = FJKIXWOMBXYWOQ-UHFFFAOYSA-N | SMILES = CCOC=C }} |Section2={{Chembox Properties | C=4|H=8|O=1 | MolarMass = | Appearance = colorless liquid | Density = 0.7589 g/mL | MeltingPtC = −116 | BoilingPtC = 33 | Solubility = 8.3 g/L at 15°C }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPtC = 202 | GHSPictograms = {{GHS02}}{{GHS07}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|225|319|335|412}} | PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|273|280|303+361+353|304+340|305+351+338|312|337+313|370+378|403+233|403+235|405|501}} }} }}
'''Ethyl vinyl ether''' is an organic compound with the chemical formula CH<sub>3</sub>CH<sub>2</sub>OCH=CH<sub>2</sub>. It is the simplest enol ether that is liquid at room temperature. It is used as a synthetic building block and a monomer. 160px|thumb|left|Use of ethyl vinyl ether in the synthesis of glutaraldehyde.
==Preparation and reactions== Ethyl vinyl ether is made by reaction of acetylene and ethanol in presence of a base.<ref name=Ullm>{{Ullmann|title=Vinyl Ethers |author=Ernst Hofmann |author2=Hans‐Joachim Klimisch |author3=René Backes |author4=Regina Vogelsang |author5=Lothar Franz |author6=Robert Feuerhake |year=2011|doi=10.1002/14356007.a27_435.pub}}</ref>
The alkene portion of the molecule is reactive in many ways. It is prone to polymerization, leading to formation of polyvinyl ethers. Polymerization is typically initiated with Lewis acids such as boron trifluoride.<ref>{{Ullmann|title=Poly(Vinyl Ethers)|author=Gerd Schröder|year=2012|doi=10.1002/14356007.a22_011}}</ref>
Ethyl vinyl ether participates in many reactions of interest to organic synthesis.<ref name=eEROS>{{cite journal|journal=EEROS|title=Ethyl Vinyl Ether|author=Percy S. Manchand|year=2001|doi=10.1002/047084289X.re125|isbn=0-471-93623-5}}</ref> With catalytic amounts of acids, ethyl vinyl ether adds to alcohols to give the mixed acetal: :EtOCH=CH<sub>2</sub> + ROH → EtOCH(OR)CH<sub>3</sub> This alcohol protection reaction is akin to the behavior of dihydropyran.
Ethyl vinyl ether also participates in inverse demand [4+2] cycloaddition reactions.
Deprotonation with butyl lithium gives the acetyl anion equivalent: :EtOCH=CH<sub>2</sub> + BuLi → EtOC(Li)=CH<sub>2</sub> + BuH
==Toxicity== The toxicity of vinyl ethers has been heavily investigated because they have been used as inhalation anesthetics. The acute {{LD50}} for the closely related methyl vinyl ether is greater than 4 g/kg (rats, oral).<ref name=Ullm/>
== References == {{reflist}}
Category:Vinyl ethers Category:Ethyl compounds