Реакция #446931

Уравнение реакции

ammonium chloride

N-Butyllithium

2-methylthiophene

oxetane

→

title compound

Выход 17.6%

5-Methyl-2-thienylpropanol

Выход 17.6%

Растворители

hexane

THF

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 22.5 h
3. 3
   Экстракцияthe mixture extracted with diethyl ether (3×200 ml)
4. 4
   Другоеdried
5. 5
   Другоеevaporated in vacuo
6. 6
   Другоеto give an oil
7. 7
   ДругоеPurification by FCC on silica gel with cyclohexane-diethyl ether (1:1) as eluent

Методика

N-Butyllithium in hexane (1.5M; 35.6 ml) was added dropwise at room temperature under nitrogen to a solution of 2-methylthiophene (5.0 g) in dry THF (50 ml). After stirring for 2.25 h, oxetane (4.42 g) in dry THF (15 ml) was added dropwise and stirring continued for 22.5 h. Saturated ammonium chloride solution (200 ml) was added and the mixture extracted with diethyl ether (3×200 ml), dried and evaporated in vacuo to give an oil. Purification by FCC on silica gel with cyclohexane-diethyl ether (1:1) as eluent gave the title compound as a pale orange oil (1.4 g). T.l.c. (cyclohexane-diethyl ether 1:1) Rf 0.31.

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