Reacción #446931

Ecuación de reacción

ammonium chloride

N-Butyllithium

2-methylthiophene

oxetane

→

title compound

Rendimiento 17.6%

5-Methyl-2-thienylpropanol

Rendimiento 17.6%

Disolventes

hexane

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 22.5 h
3. 3
   Extracciónthe mixture extracted with diethyl ether (3×200 ml)
4. 4
   Otrodried
5. 5
   Otroevaporated in vacuo
6. 6
   Otroto give an oil
7. 7
   OtroPurification by FCC on silica gel with cyclohexane-diethyl ether (1:1) as eluent

Procedimiento

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.

Fuente