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Ethoxyacetylene is used in Arens-van Dorp synthesis to prepare propargyl alcohol via reaction with ketone. In organic synthesis, it undergoes [2+2] cycloaddition reactions with ketenes to give cyclobutenone derivatives. It is also used to prepare alpha, beta-unsaturated esters from ketones by following Meyer-Schuster rearrangement.Used with N-vinylamides and triflic anhydride in a direct, three-component synthesis of pyridines. Also used to prepare α, β-unsaturated esters from ketones via a Meyer-Schuster rearrangement.
Supplied in solution to reduce polymerization. Quantities offered relate to gross weight of solution.
Undergoes [2+2] cycloaddition reactions with ketenes to give cyclobutenone derivatives: J. Org. Chem., 38, 1451 (1973).
Adds to carbonyl compounds in the presence of ZnBr2: Can. J. Chem., 54, 2310 (1976).
The Grignard reagent, prepared by exchange with ethyl magnesium bromide, adds to carbonyl compounds to give carbinols which rearrange in acid to ɑß-unsaturated acids. Alternatively, partial reduction of the adduct followed by hydrolysis provides a route to ɑß-unsaturated aldehydes: J. Chem. Soc., 1823 (1949); Rec. Trav. Chim., 82, 305 (1963):
Rearrangement by BF3 etherate leads directly to the ethyl ester: Rec. Trav. Chim., 78, 664 (1959); Chem. Lett., 1129 (1981); 241, 1271 (1982). See also Chloroacetaldehyde diethyl acetal, L07661.
Has been used as a mild dehydrating agent in peptide synthesis: Rec. Trav. Chim., 77, 1153 (1958), and for conversion of sensitive dicarboxylic acids to their anhydrides: J. Org. Chem., 33, 3808 (1968).
Aleman, G. H. J.; Machado, R. A. R.; Gorls, H.; Baldwin, I. T.; Bolan, W. Synthesis, structural characterization and biological activity of two diastereomeric JA-Ile macrolactones. Org. Biomol. Chem. 2015, 13 (21), 5885-5893.
Henry, C.; Bolien, D.; Ibanescu, B.; Bloodworth, S.; Harrowven, D. C.; Zhang, X.; Craven, A. Generation and Trapping of Ketenes in Flow. Eur. J. Org. Chem. 2015, 2015 (7), 1491-1499.
Hazard Statements: H225-H303-H315-H361-H373-H304
Highly flammable liquid and vapour. May be harmful if swallowed. Causes skin irritation. Suspected of damaging fertility or the unborn child. May cause damage to organs through prolonged or repeated exposure. May be fatal if swallowed and enters airways.
Precautionary Statements: P210-P273-P280h-P281-P301+P330+P331-P315
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid release to the environment. Wear protective gloves/clothing. Use personal protective equipment as required. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Get immediate medical advice/attention.