تفاعل #2139967

معادلة التفاعل

triflate

2-chloro-4-t-butylphenyl trifluoromethane-sulfonate

1,3-diphenylphosphinopropane

methanol

triethylamine

dimethylformamide

→

methyl 2-chloro-4-t-butylbenzoate

المذيبات

carbon monoxide

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter leaving the reaction mixture
2. 2
   درجة الحرارةto cool
3. 3
   استخلاصfollowed by the extraction with ethyl acetate/hexane
4. 4
   أخرىthe 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