تفاعل #2139968

معادلة التفاعل

hydrochloric acid

ester

methyl 2-chloro-4-t-butylbenzoate

diisobutylaluminum hydride

→

2-chloro-4-t-butylbenzyl alcohol

المردود 51.0%

المذيبات

toluene

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىwas elevated to room temperature
2. 2
   استخلاصAfter the extraction with ethyl acetate
3. 3
   أخرىfollowed by the purification by the silica gel column chromatography

الإجراء التجريبي

The triflate compound (638 mg, 2 mmol) obtained in Step 1-2, palladium acetate (14 mg), 1,3-diphenylphosphinopropane (25 mg), methanol (4 ml) and triethylamine (0.6 ml) were dissolved in dimethylformamide (5 ml), and the obtained solution was stirred at 80° C. in carbon monoxide atmosphere for 16 hours. After leaving the reaction mixture to cool followed by the extraction with ethyl acetate/hexane and the purification by the silica gel column chromatography, methyl 2-chloro-4-t-butylbenzoate was obtained. The ester thus obtained was dissolved in dichloromethane (2 ml). 1 M solution (2.5 ml) of diisobutylaluminum hydride in toluene was added dropwise to the obtained solution at −78° C. in argon atmosphere, and the resulting solution was stirred at that temperature for 5 minutes. 0.5 M hydrochloric acid (20 ml) was added to the reaction mixture, and the temperature was elevated to room temperature. After the extraction with ethyl acetate followed by the purification by the silica gel column chromatography, 2-chloro-4-t-butylbenzyl alcohol (yield: 204 mg, 51%) was obtained.

المصدر