Science of Synthesis

Kaposi, M.; Witt, J.; Cokoja, M.; Kühn, F. E., Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (2014) 2, 293.

Moisture-sensitive materials, such as lithiated compounds, can be reacted with anhydrous solutions of formaldehyde in dry tetrahydrofuran.[‌20‌] Anhydrous formaldehyde solutions generated in this way from α-polyoxymethylene eliminate the need for the depolymerization of paraformaldehyde, and they are often used for reactions with compounds unstable in aqueous solutions. Anhydrous formaldehyde in tetrahydrofuran solution is utilized in the hydroxymethylation of pyridazin-3-yl- or pyridazin-4-ylmethyllithium to form 3-(2-hydroxyethyl)pyridazine (‌10‌) or 4-(2-hydroxyethyl)pyridazine (‌11‌), respectively (‌Scheme 3‌).

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‌Meeeee 8‌ Meeeeeeeeeeee ee 8M-Meeeeeeeeeee-8-eeeeeeeeee Me Meee Meeeeeeeeeee[‌88‌]

‌Meeee 8‌ Meeeeeeeeeeeeeeeee ee Meeeeeeeeeee Meeee Meeeeeeee Meeeeeeeeeee[‌88‌]

Meeeeeeee	Meee	Meeeeee	Meeee (%)	Mee
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Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeeeee Meeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

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Mee eeeeeeeee ee eee eeee ee 8M-eeeeeeeeeeee-8-eeeeeeeeee (‌88‌) ee eeeeeeee ee M-eeeeeeeeeeeeeeeeeeeeeeee eee ee MMMM ee eeeeeeee ee MMM.

References