반응 #457867

반응 방정식

p-[(trimethylsilyl)ethynyl]-phenol

potassium hydroxide

→

p-ethynylphenol

수율 88.0%

용매

methanol

반응 조건

후처리

1. 1
   기타Methanol was subsequently removed on a rotary evaporator
2. 2
   workup.ADDITIONthe residue, after the addition of 30 ml of 1N hydrochloric acid
3. 3
   추출was extracted three times with 30 ml of diethyl ether each time
4. 4
   세척The organic phases were washed twice with 30 ml of water each time
5. 5
   건조once with 30 ml of saturated sodium chloride solution, dried over magnesium sulphate
6. 6
   농축concentrated

실험 절차

A solution of 382 mg of p-[(trimethylsilyl)ethynyl]-phenol (prepared according to Example 10) in 15 ml of a 1:1 mixture of methanol and 1N aqueous potassium hydroxide solution was stirred at room temperature for 45 minutes in a round flask under argon gasification. Methanol was subsequently removed on a rotary evaporator and the residue, after the addition of 30 ml of 1N hydrochloric acid, was extracted three times with 30 ml of diethyl ether each time. The organic phases were washed twice with 30 ml of water each time and once with 30 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. There were obtained 207 mg (88%) of p-ethynylphenol as a colourless oil (decomposing rapidly in the pure state) which was taken up immediately in 50 ml of diethyl ether and treated with 436 mg of trans-4-pentylcyclohexanecarboxylic acid, 454 mg of N,N'-dicyclohexylcarbodiimide and 24.4 mg of 4-(dimethylamino)pyridine. This mixture was stirred at room temperature for 18 hours and subsequently filtered. The filtrate was treated with 50 ml of water and extracted three times with 50 ml of diethyl ether each time. The organic phases were washed with 50 ml of water and with 50 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.4 bar) of the residue (847 mg) on silica gel with 3% ethyl acetate petroleum ether gave 277 mg (46%) of trans-4-pentylcyclohexanecarboxylic acid p-ethynylphenyl ester as colourless crystals (purity 98.5%) which were recrystallized further from methanol (purity 99.1%); m.p. (C-N) 50.6° C., cl.p. (N-I) 78.5° C.

출처