Diethyl Ether → HCID 15204724, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 28.3 g (0.15 mol) of o-bromobenzyl alcohol in 1 L of ether cooled to -20° C. was added in portions 32.5 ml (0.32 mol) of n-butyllithium (10M) in hexane over a 20 min period and the reaction mixture was stirred for 1 hr. The above reaction mixture was cooled to -20° C., 19.9 g (0.165 mol) of 6-methyl-2-pyridinecarboxaldehyde was added to the mixture, and the resulting reaction mixture was allowed to warm to room temperature. After 1 hour, ammonium chloride solution was added to the mixture. The diol was extracted with ethyl acetate, washed with brine, the ethyl acetate phase was dried over sodium sulfate, and the solvent was removed in vacuo to afford 21.9 g (70.5%) of 2-[1-hydroxy-(2'-hydroxymethyl)-benzyl]-6-methyl-pyridine (Formula XIII: R1 =6--CH3 ; R2 =R7 =H).

Provenance & Evidence