Ethanolamine → 3-Benzyloxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one

Participants

Reaction Steps

3-Benzyloxy-2-methyl-4-pyrone, prepared as described under (J), is reacted with 1-amino-5-hydroxypentane under substantially similar conditions to those described under (K) for reaction with 2-hydroxyethylamine to give 3-benzyloxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one. This is deprotected using the procedure described under (I) to give 3-hydroxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one as white crystals, m.p. 136°-138° C.; δmax (nujol) 1625, 3350 cm-1 : δ(d6DMSO) 1.3 (m, 6H), 2.40 (s, 3H), 3.25 (t, 2H), 4.20 (t, 2H), 7.20 (d, 1H), 8.15 (d, 1H).

Provenance & Evidence