Triethylsilane → 4-Chloro-2-(4-ethylbenzyl)phenol

反応式

[SiH](CC)(CC)CC.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([OH:25])=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=2)=O)[CH:14]=1.C(S(O)(=O)=O)(F)(F)F>C(O)(C(F)(F)F)=O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([OH:25])=[C:13]([CH2:15][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH3:24])=[CH:21][CH:22]=2)[CH:14]=1

参加物

実験手順

To a stirred 0° C. solution of Et3SiH (2.26 ml, 14.2 mmol) and (5-chloro-2-hydroxyphenyl)(4-ethylphenyl)methanone (1.944 g, 7.08 mmol) in 10 mL of TFA was added CF3SO3H (30 μL) at a rate to keep the temperature at about 0° C. After complete addition, the mixture was warmed to room temperature and stirred overnight at room temperature. After the volatiles were evaporated under reduced pressure, the residue was partitioned in ethyl acetate and water. The organic layer was separated and washed with water, aq Na2CO3, brine then dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (PE:EA=10:1) to give the target compound (1.659 g).