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Triethyl orthoacetate is used as pharmaceutical and water scavenger. It is also used in organic synthesis to introduce the acetate group into an alcohol. It is involved in the Johnson-Claisen rearrangement.
Reagent for facile esterification of sulfonic and carboxylic acids: Tetrahedron Lett., 34, 7355 (1993).
The products with allylic alcohols undergo Claisen allyl ether rearrangement, with addition of a 2-carbon unit and repositioning of the double bond: J. Am. Chem. Soc., 92, 741 (1970); Tetrahedron Lett., 21, 1285 (1980):
For further examples, see: Org. Synth. Coll., 6, 584 (1988); 7, 164 (1990).
Reaction with BF3 etherate gives the moderately stable selective alkylating agent, methyl diethoxycarbenium tetrafluoroborate: Synth. Commun., 19, 2307 (1989). Compare Triethyl orthoformate, A13587.
Under mild acid catalysis, reacts with ethynyl alcohols to give allenic esters, which can be conjugated over alumina. For examples, see: Org. Synth. Coll., 8, 251 (1993):
Yang, J.; Su, G.; Ren, Y.; Chen, Y. Design, synthesis and evaluation of isoxazolo [5, 4-d] pyrimidin-4 (5H)-one derivatives as antithrombotic agents. Bioorg. Med. Chem. Lett. 2015, 25 (3), 492-495.
Shawali, A. S.; Sami, A. Annulated 3-Amino-4-Imino-Pyrimidines: Their Utility as Useful Precursors for the Synthesis of Fused Heterocycles. Curr. Org. Synth. 2015, 12 (4), 391-430.
Hazard Statements: H226-H315-H319
Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation.
Precautionary Statements: P210-P233-P240-P241-P242-P243-P264b-P280-P303+P361+P353-P305+P351+P338-P332+P313-P337+P313-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant