反应详情

温度

-40 °C

2-(3-Trifluoromethylphenyl)-furan (J. Chem. Soc. (C) 1968, 2737 and Acta Chem Scand. 24, 2379 (1970))(21.2 g; 0.1 mole) was stirred in tetrahydrofuran (100 ml), cooled to -40° C. and n-butyl lithium (0.1 mole, solution in hexane) was added dropwise. After stirring for 1 hour at -40° C., paraformaldehyde (3.3 g; 0.11 mole) was added gradually. The mixture was stirred at -40° C. for 30 minutes, then the temperature was allowed to rise. At 10° C. an exothermic reaction set in and the temperature gradually rose to 40° C. (over 10 minutes), then gradually fell back to 20° C. After stirring for further 1 hour the clear brown solution was poured onto ice/water, adjusted to pH ca 4 with dilute hydrochloric acid and extracted via ethyl acetate. The dried acetate extract (MgSO4) was evaporated to give a brownish yellow viscous oil which was distilled in vacuo to give 2-hydroxymethyl-5-(3-trifluoromethylphenyl)-furan as a colourless liquid b.p. 125° C./0.5 mm., (16.2 g), which on standing gave crystals, m.p. 45° C.

1. stirringThe mixture was stirred at -40° C. for 30 minutes
2. customAt 10° C. an exothermic reaction
3. customgradually rose to 40° C.
4. custom(over 10 minutes)
5. customgradually fell back to 20° C
6. stirringAfter stirring for further 1 hour the clear brown solution
7. additionwas poured onto ice/water
8. extractionextracted via ethyl acetate
9. extractionThe dried acetate extract (MgSO4)
10. customwas evaporated
11. customto give a brownish yellow viscous oil which
12. distillationwas distilled in vacuo