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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1728071Generated: October 30, 2026

Acetyl chloride → 3-Trimethylsilyoxy-2-aza-1,3-butadiene

https://huagongshe.com/reaction/1728071

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetyl chlorideHCID 6367—
ReactantChlorotrimethylsilaneHCID 6397—
ReactantTriethylamineHCID 8471—
ReactantHexamethyldisilazaneHCID 13838—
Reactant2-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehydeHCID 57565916—
ReactantButyllithiumHCID 178418339—
Product3-Trimethylsilyoxy-2-aza-1,3-butadieneHCID 86617594—

Reaction Steps

In a manner similar to the method described in example 1b, 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehyde (5.2 g, 17 mmol) prepared in example 131a was reacted with 1,1,1,3,3,3-hexamethyldisilazane (2.4 g, 15 mmol), n-butyllithium (2.5 M, 6 mL, 15 mmol), trimethylsilyl chloride (1.6 g, 15 mmol), triethylamine (1.6 g, 20 mmol) and acetyl chloride (1.5 g, 20 mmol) to give 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene as yellow oil and used for the next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07495007B2
Source datasetuspto-grants-2009_02
ORD IDord-aa111af147fa40a2b9e46e0b58cbe7c2
Source noteuspto-grants-2009_02