Henze, Henry R. published the artcileHydantoins containing a tetrahydropyranyl substituent, Computed Properties of 30431-99-3, the publication is Journal of the American Chemical Society (1942), 1672-4, database is CAplus.
Refluxing a mixture of 155 g. NCCH2CO2Et and 97 g. (ClCH2CH2)2O with 31.5 g. of Na in 450 cc. EtOH for 3 h. gives 31% of the Et ester, b16 135°, nD20 1.4539, d420 1.1109, γ20 37.4, of 4-cyanotetrahydro-4-pyrancarboxylic acid; heating the acid at 180-200° gives 90% of tetrahydro-4-pyrancarbonitrile (I), b10 82-3°, nD20 1.4521, d420 1.0343, γ20 40.7. 4-Acyltetrahydropyrans, RCOCH(CH2.CH2)2O, were prepared by addition of a mol. proportion of I in absolute ether to 1.2-2 M proportions of the Grignard reagent (R is given): Me, b144 205-7°, nD20 1.4530, d420 1.0243, γ20 35.8, MR 33.98, 53% yield (semicarbazone, m. 178° (all m. ps. corrected)); Et, b20 101°, n 1.4541, d. 1.0016, γ 37.2, MR, 38.60, 72% (semicarbazone, m. 151°); Pr, b5 85-8°, n 1.4545, d. 0.9828, 57% (semicarbazone, m. 145-6°); Bu, b5 100°, n 1.4551, d. 0.9700, 67% (semicarbazone, m. 180°; 2,4-dinitrophenylhydrazone, m. 99°); iso-Bu, b6 90-2°, n 1.4545, d. 0.9648, γ 33.2, MR 47.83, 69% (semicarbazone, m. 187-8°; 2,4-dinitrophenylhydrazone, m. 122°); Am, b5 106-7°, n 1.4573, d. 0.9589, γ 33.3, MR 52.45, 64% (semicarbazone, m. 117°; 2,4-dinitrophenylhydrazone, m. 89-90°); iso-Am, b7 116-17°, n 1.4567, d. 0.9562, γ 32.9, MR 52.45, 65% (semicarbazone, m. 158-9°; 2,4-dinitrophenylhydrazone, m. 134-5°); hexyl, b6 134-5°, n 1.4569, d. 0.9446, MR 57.07, 61% (semicarbazone, m. 161°); cyclohexyl, b5 142°, n 1.4839, d. 1.0262, MR 54.87, 46% (semicarbazone, m. 213-14°); Ph, m. 57-8°, 67%. The ketone with 1.8 molar equivalents of KCN and 3.6 molar equivalents of (NH4)2CO3 in about 150 cc. 50% EtOH heated 12 h. at 58-60° gives 5-substituted 5-(tetrahydro-4-pyranyl)hydantoins, HN.CO.NH.CO.CRCH(CH2.CH2)2O (R given): Me, m. 250°, 51%; Et, m. 246°, 70%; Pr, m. 223°, 66%; Bu, m. 195°, 49%; iso-Bu, m. 222°, 53%; Am, m. 171-2°, 79%; iso-Am, m. 195-6°, 68%; hexyl, m. 169°, 48%; cyclohexyl, m. 304-6°, 65%; Ph, m. 253°, 72%. The iso-Am and Ph derivatives exhibit mild anticonvulsant activity and are devoid of any hypnotic action.
Journal of the American Chemical Society published new progress about 30431-99-3. 30431-99-3 belongs to nitriles-buliding-blocks, auxiliary class Tetrahydropyran,Nitrile,Ester, name is Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate, and the molecular formula is C9H13NO3, Computed Properties of 30431-99-3.
Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts