3-Methyl-2-cyclopenten-1-one → 1-Tert-butyl-3-methylcyclopenta-1,3-diene

온도

0 °C

In a nitrogen atmosphere, dehydrated diethylether (350 ml) was added to a tert-butylmagnesium chloride/diethyl ether solution of 2.0 mol/lit. concentration (450 ml, 0.90 mol) to thereby obtain a solution. A solution of 3-methylcyclopentenone (43.7 g, 0.45 mmol) in dehydrated diethyl ether (150 ml) was dropped into the above solution while maintaining its temperature at 0° C. by cooling with ice. The mixture was agitated at room temperature for 15 hr. A solution of ammonium chloride (80.0 g, 1.50 mol) in water (350 ml) was dropped into the reaction mixture while maintaining its temperature at 0° C. by cooling with ice. Water (2500 ml) was added to the obtained solution, and agitated. An organic layer containing the reaction product was separated and washed with water. A 10% aqueous hydrochloric acid solution (82 ml) was added to the organic layer while maintaining its temperature at 0° C. by cooling with ice, and agitated at room temperature for 6 hr. The organic layer of the reaction mixture was separated, washed with water, a saturated aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride in sequence, and dried over anhydrous magnesium sulfate (drier). The drier was filtered off, and the solvent was distilled off from the filtrate. Thus, a liquid was obtained. 14.6 g of light-yellow liquid (1-tert-butyl-3-methylcyclopentadiene) was obtained by vacuum distillation (45 to 47° C./10 mmHg) of the above liquid. The analytical value thereof was as follows:

1. customto thereby obtain a solution
2. temperatureby cooling with ice
3. temperaturewhile maintaining its temperature at 0° C.
4. temperatureby cooling with ice
5. stirringagitated
6. additionAn organic layer containing the reaction product
7. customwas separated
8. washwashed with water
9. additionA 10% aqueous hydrochloric acid solution (82 ml) was added to the organic layer
10. temperaturewhile maintaining its temperature at 0° C.
11. temperatureby cooling with ice
12. stirringagitated at room temperature for 6 hr
13. customThe organic layer of the reaction mixture was separated
14. washwashed with water
15. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride in sequence, and dried over anhydrous magnesium sulfate (drier)
16. filtrationThe drier was filtered off
17. distillationthe solvent was distilled off from the filtrate
18. customThus, a liquid was obtained

ORD 기록

ord-959d841c60e0480689dc6ba6a7085062

출처 데이터셋

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07619030B2