2020•Russian Journal of General ChemistryRequires access

Condensation of Propan-2-one with Formaldehyde and Propane-2-thiol

Л. А. Баева, Р. М. Нугуманов, Л. Ф. Бикташева, Р. Л. Сафиуллин

Abstract

Abstract Three-component condensation of propan-2-one with formaldehyde and propane-2-thiol in the presence of sodium hydroxide afforded 3-{[(propan-2-yl)sulfanyl)]methyl}but-3-en-2-one or 4-[(propan-2-yl)sulfanyl]-3-{[(propan-2-yl)sulfanyl]methyl}butan-2-one, depending on the amount of the base. The formation of 4-[(propan-2-yl)sulfanyl]-3-{[(propan-2-yl)sulfanyl]methyl}butan-2-one from 4-[(propan-2-yl)sulfanyl]butan-2-one involved aldol condensation of the latter with formaldehyde and subsequent nucleophilic addition of propane-2-thiol to the C=C double bond of intermediate 3-{[(propan-2-yl)sulfanyl]methyl}but-3-en-2-one in the presence of sodium hydroxide.

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Key concepts: Sulfanyl, Chemistry, Propane, Thiol, Medicinal chemistry, Formaldehyde, Nucleophile, Sodium hydroxide