反応 #216448

反応方程式

ether

3-(1-hydroxy-2,2,2-trifluoroethyl)-3-n-propyloxetane

pyridine

diethyl ether

→

2,2,2-trifluoro-1-(3-propyloxetan-3-yl)ethyl hex-5-ynoate

反応条件

後処理

1. 1
   workup.ADDITIONadded
2. 2
   洗浄After washing with water, dilute hydrochloric acid, saturated sodium bicarbonate solution and brine
3. 3
   乾燥the organic phase was dried over anhydrous magnesium sulphate
4. 4
   その他evaporated in vacuo
5. 5
   その他The residue was purified by chromatography on silica
6. 6
   洗浄pre-eluted with hexane containing 1% triethylamine
7. 7
   洗浄Gradient elution with hexane/ether mixtures

実験手順

A mixture of hex-5-ynoic acid (1 g) and thionyl chloride (1.95 ml) in benzene (25 ml) was heated at reflux for 2.5 hours. The resulting solution was cooled and then evaporated in vacuo. The acid chloride thus obtained was taken up in dry diethyl ether (5 ml) and added, dropwise, to a stirred solution of 3-(1-hydroxy-2,2,2-trifluoroethyl)-3-n-propyloxetane (1.77 g) (European Patent Application No. 211598) and pyridine (0.8 ml) in ether (20 ml). The reaction mixture was allowed to stir at room temperature overnight. After washing with water, dilute hydrochloric acid, saturated sodium bicarbonate solution and brine, the organic phase was dried over anhydrous magnesium sulphate and then evaporated in vacuo. The residue was purified by chromatography on silica, pre-eluted with hexane containing 1% triethylamine. Gradient elution with hexane/ether mixtures gave 2,2,2-trifluoro-1-(3-propyloxetan-3-yl)ethyl hex-5-ynoate (1.2 g) as a colourless oil.

出典