Réaction #1552107

Équation de réaction

water

n-butyl lithium

3-[(tert-butyldimethylsilyl)oxy]pyridin-2(1H)-one

3-(tert-butyldimethylsilanyloxy)-1H-pyridin-2-one

4-methylbenzenesulfonyl chloride

→

desired compound

1-(4′-Methylbenzenesulfonyl)-3-hydroxypyridin-2(1H)-one

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Températureto warm to room temperature over one hour
2. 2
   Extractionthe contents of the reaction vessel is extracted with EtOAc (3×)
3. 3
   Lavagewashed with brine (1×)
4. 4
   Séchagedried over Na2SO4
5. 5
   Concentrationconcentrated
6. 6
   SéchageThe combined organic layers are dried over Na2SO4
7. 7
   Concentrationconcentrated
8. 8
   workup.ADDITIONtreated with conc. HCl (2 mL)
9. 9
   Autrethe solvent is removed under reduced pressure

Mode opératoire

To stirred solution of 3-[(tert-butyldimethylsilyl)oxy]pyridin-2(1H)-one (1) (4.66 g, 20.7 mmol) in dry THF (150 mL), maintained at −78° C. under a dry nitrogen atmosphere is added n-butyl lithium (1.6 M solution in hexane, 21.0 mmol). After 20 minutes, 4-methylbenzenesulfonyl chloride (3.95 g, 20.7 mmol) is added as a THF solution. The solution is allowed to warm to room temperature over one hour, the water (10 mL) is added and the contents of the reaction vessel is extracted with EtOAc (3×), washed with brine (1×), dried over Na2SO4 and concentrated. The combined organic layers are dried over Na2SO4 and concentrated. The residue is taken up in ethanol (10 mL) and treated with conc. HCl (2 mL). The mixture is allowed to stir for 1 hour and the solvent is removed under reduced pressure to afford the desired compound as a white solid. 1H NMR (300 MHz, DMSO) δ 2.43 (s, 3H), 6.14 (t, J=6.9 Hz, 1H), 6.76 (dd, J=7.65 Hz, 1.5 Hz, 1H), 7.18 (dd, J=6.6 Hz, 1.8 Hz, 1H), 7.32 (d, J=7.3 Hz, 2H), 7.98 (d, J=7.9 Hz, 2H).

Source