3-Trimethylsilyl-3-buten-2-one

CAS 43209-86-5, Cat. No EN300-7170326
Reagent for annulation reaction

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3-Trimethylsilyl-3-buten-2-one is a versatile α-silylated vinyl ketone used as a Michael acceptor in annulation reactions, Peterson condensations, and γ,δ-unsaturated ketone synthesis¹. It plays a key role in Robinson annulations, forming bicyclic and polycyclic ketones with high efficiency. The reagent undergoes regioselective Michael additions with enolates, organocuprates, and Grignard reagents, making it valuable for complex molecule synthesis. It also participates in Diels–Alder reactions after conversion to a bis(trimethylsilyl) diene. This stable liquid has a boiling point of 72°C at 50 mmHg and can be stored under argon at −20°C without degradation.

Synonyms: 3-buten-2-one, 3-(trimethylsilyl)-; 3-trimethylsilylbut-3-en-2-one; 3-(trimethylsilyl)-3-buten-2-one; methyl 1-trimethylsilylvinyl ketone; 1-(trimethylsilyl)-vinyl methyl ketone