Tetrahydro-pyran-3-carbaldehyde

Uses

Tetrahydro-pyran-3-carbaldehyde is a key intermediate for the synthesis of a novel 5-lipoxygenase inhibitor. Also it is a reactant used to synthesize tetrahydropyran esters as attractant toward Blattella germanica and Supella longipalpa.

Synthesis

General procedure for the synthesis of tetrahydropyran-3-carbaldehyde from 5,6-dihydro-2H-pyran-3-carbaldehyde: 10% Pd/C catalyst (600 mg) was slowly added to a solution of 5,6-dihydro-2H-pyran-3-carbaldehyde (6 g, 53.5 mmol) in methanol (10 mL). The reaction mixture was stirred under hydrogen (40 psi) atmosphere. Upon completion of the reaction, the reaction mixture was filtered through diatomaceous earth, the precipitate was washed with methanol and the filtrate was concentrated under vacuum. The residue was purified by fractional distillation at 125°C/20 mmHg to afford tetrahydropyran-3-carbaldehyde (5.5 g, 91.6% yield). Mass spectral (MS) data (m/z): [M + H]+, 115.1.

References

[1] Molecular Pharmacology, 2015, vol. 87, # 3, p. 477 - 491
[2] Patent: WO2016/85939, 2016, A2. Location in patent: Paragraph 00260
[3] Patent: US5071863, 1991, A
[4] Chemistry and Industry (London, United Kingdom), 1955, p. 1772