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Synlett 2025; 36(05): 508-511
DOI: 10.1055/a-2421-3288
letter

Selection of Conditions for the Synthesis of Methacrylate Monomers Based on Adamantane

Alexander S. Novikov  ∗
,
Georgiy V. Malkov
,
Alexander V. Akkuratov
This work was funded by the Ministry of Science and Higher Education of the Russian Federation (Project No. 122111700041-8 and 124020800013-7).
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Abstract

Adamantane-based methacrylates are important monomers for the design of polymers used for the development of chemically amplified photoresists. Herein, we present the selection of reaction conditions for obtaining of 2-ethyladamantan-2-yl methacrylate, 2-methyladamantan-2-yl methacrylate, adamantan-1-yl methacrylate, and 3-hydroxyadamantan-1-yl methacrylate from adamantane derivatives and methacryloyl chloride. It is shown that the combination of pyridine as a solvent and base with 1,4-diazabicyclo[2.2.2]octane (DABCO) as a base allows reproducible preparation of the desired products with good yields. The results obtained provide valuable information for upscaling the synthesis of important products for the microelectronics industry.

Key words

DUV photolithography - photoresist monomers - adamantyl methacrylates - reaction conditions - DABCO - acylation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2421-3288.
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Publication History

Received: 07 August 2024

Accepted after revision: 24 September 2024

Accepted Manuscript online:
24 September 2024

Article published online:
22 October 2024

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