반응 #2028901

반응 방정식

n-butyllithium

p-toluenesulfonyl chloride

THF

n-Butyllithium

THF

→

2-(trans-4-propyl-cyclohexyl)-oxetane

수율 70.0%

반응 조건

후처리

1. 1
   기타prepared in the third step in a reaction vessel under an atmosphere of nitrogen
2. 2
   workup.STIRRINGAfter the reaction mixture had been stirred for 30 minutes
3. 3
   온도the reaction mixture was heated slowly up to the reflux temperature
4. 4
   기타quenched with a saturated aqueous solution of ammonium chloride
5. 5
   workup.ADDITIONwater (1,000 ml) was added
6. 6
   기타to give two layers
7. 7
   추출The water layer was extracted with toluene (500 ml) three times
8. 8
   세척the combined organic layer was washed with water
9. 9
   건조dried over anhydrous magnesium sulfate
10. 10
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure
11. 11
    workup.ADDITIONThe residue was treated with silica gel chromatography (silica gel: 200 g, eluent: heptane/ethyl acetate=90/10 by volume)
12. 12
    workup.DISTILLATIONdistilled under reduced pressure (71 to 74° C., 3 mmHg)

실험 절차

THF (1,000 ml) was added to 1-(trans-4-propyl-cyclohexyl)-propane-1,3-diol(4) (229.3 g) prepared in the third step in a reaction vessel under an atmosphere of nitrogen. n-Butyllithium (1.63 M in n-hexane; 702 ml) was added dropwise to the mixture at around −5° C. After 30 minutes of stirring, p-toluenesulfonyl chloride (218.2 g) in a THF (1,000 ml) solution was added dropwise. After the reaction mixture had been stirred for 30 minutes, n-butyllithium (1.63 M in n-hexane; 702 ml) was added dropwise at around −5° C., and then the reaction mixture was heated slowly up to the reflux temperature. After the evolution of gas had ceased, the reaction mixture was cooled to room temperature, and quenched with a saturated aqueous solution of ammonium chloride, and then water (1,000 ml) was added to give two layers. The water layer was extracted with toluene (500 ml) three times, and the combined organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was treated with silica gel chromatography (silica gel: 200 g, eluent: heptane/ethyl acetate=90/10 by volume) and distilled under reduced pressure (71 to 74° C., 3 mmHg) to give 2-(trans-4-propyl-cyclohexyl)-oxetane (5) (145 g) in 70% yield.

출처