反応 #9342

反応方程式

diisobutylamine

Diisobutylamine

6-hydroxy-7-propyl-3-trifluoromethylbenzisoxazole

sodium bisulfite

benzisoxazole

sulfuryl chloride

→

title compound

5-Chloro-6-hydroxy-7-propyl-3-trifluoromethyl-1,2-benzisoxazole

溶媒

toluene

ethyl ether

反応条件

後処理

1. 1
   その他results in a suspension which
2. 2
   その他The phases were separated
3. 3
   洗浄The ether phase was washed with brine
4. 4
   乾燥dried over Na2SO4
5. 5
   その他The solvent was evaporated in vac
6. 6
   その他to give an orange solid which
7. 7
   その他was purified by chromatography on silica gel eluting with acetone:hexane (2:98)

実験手順

Diisobutylamine (0.8 ml, 0.10 eq) and 6-hydroxy-7-propyl-3-trifluoromethylbenzisoxazole (11 gm, 1.0 eq) were dissolved in toluene (275 ml) at room temperature. Slow addition of sulfuryl chloride (4.20 ml, 1.15 eq) results in a suspension which was stirred overnight. Additional diisobutylamine (total 1.6 ml, 0.4 eq) was added in four equal portions over 24 hr until no further starting benzisoxazole was detected by analytical TLC. The reaction mixture was poured into saturated sodium bisulfite (500 ml) and ethyl ether (700 ml). The phases were separated. The ether phase was washed with brine and dried over Na2SO4. The solvent was evaporated in vac to give an orange solid which was purified by chromatography on silica gel eluting with acetone:hexane (2:98) to give the title compound.

出典