Sodium Hydroxide → (6-Methylpyridin-3-yl)acetic acid

반응식

[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9](N2CCOCC2)=S)=[CH:4][CH:3]=1.[OH-:17].[Na+].[OH2:19].CCO>>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:19])=[O:17])=[CH:4][CH:3]=1

참가 물질

반응물 3

HCID 14798Sodium Hydroxide

HCID 2727779HCID 2727779, 화합물

HCID 19096565Water ethanol

생성물 1

HCID 22507698(6-Methylpyridin-3-yl)acetic acid수율 46%

실험 절차

Crude 2-(6-methyl-pyridin-3-yl)-1-morpholin-4-yl-ethanethione (39.5 mmol, 9.685 g) was suspended in 2:1 H2O/EtOH (40 mL). NaOH (3.3 eq., 118.5 mmol, 4.8 g) was added and the reaction heated to reflux for 16 hours. The volatiles were then removed from the cooled reaction medium, and the pH adjusted to precisely pH 7.0 with 3.0 M HCl. The solvent was removed and the residue slurried in boiling methanol, filtered whilst hot, and the filtrate evaporated to dryness. This crude product contains residual free morpholine, which was removed by flash column chromatography, eluting with 9:1 EtOAc/MeOH. The fractions were analysed by TLC eluting with 1:1 EtOAc/MeOH (Rf=0.209). The product was obtained in 46% yield.