反応 #1552107

反応方程式

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

溶媒

THF

THF

反応条件

後処理

1. 1
   温度to warm to room temperature over one hour
2. 2
   抽出the contents of the reaction vessel is extracted with EtOAc (3×)
3. 3
   洗浄washed with brine (1×)
4. 4
   乾燥dried over Na2SO4
5. 5
   濃縮concentrated
6. 6
   乾燥The combined organic layers are dried over Na2SO4
7. 7
   濃縮concentrated
8. 8
   workup.ADDITIONtreated with conc. HCl (2 mL)
9. 9
   その他the solvent is removed under reduced pressure

実験手順

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).

出典