反应 #2507838

反应方程式

NaOH

ethyl 4[[4-(4-ethylphenyl)-2,2-dimethyl-[2H]-thiochromen-6-yl]-ethynyl]benzoate

HCl

→

AGN194310

溶剂

THF

ethanol

反应条件

后处理

1. 1
   温度cooled to room temperature
2. 2
   其他At the beginning of the process, the reaction mixture formed a heterogeneous system
3. 3
   萃取The mixture was extracted with ethyl acetate (25 ml×2)
4. 4
   洗涤The combined organic layers were washed with 10 ml water, saturated aqueous NaCl
5. 5
   干燥dried with NaSO4
6. 6
   其他the solvent was removed under reduced pressure
7. 7
   其他The residual solid (0.31 gram) was recrystallized from acetonitrile (25 ml)

实验过程

Two ml of a 2 M solution of NaOH were added to a solution of ethyl 4[[4-(4-ethylphenyl)-2,2-dimethyl-[2H]-thiochromen-6-yl]-ethynyl]benzoate in THF and ethanol. The solution was heated to 40° C., stirred overnight, then cooled to room temperature. The reaction mixture was acidified with 1 N HCl (4 ml). At the beginning of the process, the reaction mixture formed a heterogeneous system. The mixture was extracted with ethyl acetate (25 ml×2). The combined organic layers were washed with 10 ml water, saturated aqueous NaCl, and dried with NaSO4, and the solvent was removed under reduced pressure. The residual solid (0.31 gram) was recrystallized from acetonitrile (25 ml) to yield 4-[[4-(4-ethylphenyl)-2,2-dimethyl-(2H)-thiochroman-6-yl]-ethynyl]benzoic acid, (AGN194310) (0.236 gram, 70%) as a colorless solid (m.p. 210-212° C.) [1H-NMR (DMSO-d6): d8.2 (s, 2H), d7.8 (s, 2H), d7.6 (s, 2H), d7.4 (s, 2H), d7.2 (s, 2H), d7.0 (s, 1H), d6.0 (s, 1H), d2.6 (t, 2H, J=35 Hz), d1.6 (s, 6H), d1.4 (t, 3H, J=46 Hz)].

来源