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Ethyl 2-oxo-4-(trimethylsilyl)but-3-ynoate

CAS 379224-67-6, Cat. No EN300-7500375
Reagent for cyclization

Ethyl 2-oxo-4-(trimethylsilyl)but-3-ynoate
EN300-7500375

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Ethyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is a versatile alkyne-based reagent used in heterocyclic and organosilicon chemistry. It enables the synthesis of tetrasubstituted thiophenes via [3+2] annulation with pyridinium thiolates1. The reagent also plays a key role in Bohlmann-Rahtz heteroannulation, facilitating the formation of pyrido[2,3-d]pyrimidines2,3. Air- and moisture-sensitive, it requires anhydrous conditions for handling and storage. The compound is a key reagent in asymmetric carbonyl–ene reactions, enabling the synthesis of enantioenriched α-hydroxyesters with quaternary centers4. Using a chiral N,N'-dioxide/Mg(II) catalyst, the reaction achieves up to 99% yield and >99% enantiomeric excess under mild conditions. This method is valuable for functionalized oxazole synthesis, which is relevant to biologically active compounds. The reaction is scalable to gram quantities and compatible with diverse β,γ-unsaturated α-ketoesters. The reagent is stable under standard conditions and operates efficiently at moderate temperatures (30°C).

Synonyms: ethyl 2-oxo-4-(trimethylsilyl)but-3-ynoate; 3-butynoic acid, 2-oxo-4-(trimethylsilyl)-, ethyl ester; ethyl 4-(TMS)-2-oxo-but-3-ynoate

Selected publications

  1. Synthesis of Tetrasubstituted Thiophenes from Pyridinium 1,4-Zwitterionic Thiolates and Modified Activated Alkynes.

    Wang T.; Zhu X.; Tao Q.; Xu W.; Sun H.; Wu P.; Cheng B.; Zhai H. Chinese Chemical Letters 2021, 32 (12), 3972–3975. DOI: 10.1016/j.cclet.2021.04.021

  2. A New and Highly Expedient Synthesis of Pyrido[2,3-d]Pyrimidines.

    Bagley M. C.; Hughes D. D.; Lloyd R.; Powers V. E. C. Tetrahedron Lett 2001, 42 (37), 6585–6588. DOI: 10.1016/S0040-4039(01)01297-7

  3. Synthesis of Pyridines and Pyrido[2,3-d]Pyrimidines by the Lewis Acid Catalysed Bohlmann-Rahtz Heteroannulation Reaction.

    Bagley M. C.; Dale J. W.; Hughes D. D.; Ohnesorge M.; Phillips N. G.; Bower J. Synlett 2001, (10), 1523–1526. DOI: 10.1055/s-2001-17447

  4. Catalytic Asymmetric Carbonyl-Ene Reaction of β,γ-Unsaturated α-Ketoesters with 5-Methyleneoxazolines.

    Luo W.; Zhao J.; Ji J.; Lin L.; Liu X.; Mei H.; Feng X. A Chemical Communications 2015, 51 (49), 10042–10045. DOI: 10.1039/c5cc02748a

 

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