تفاعل #487502
ord-ba3c6c58135c408d9a7c738f4e528254
معادلة التفاعل
الكواشف
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المعالجة
- 1أخرىSynthesized
- 2درجة الحرارةwas heated
- 3درجة الحرارةat reflux
- 4درجة الحرارةat reflux
- 5درجة الحرارةheating
- 6درجة الحرارةat reflux
- 7workup.WAITAfter 4 hours
- 8درجة الحرارةthe mixture was cooled to room temperature
- 9استخلاصextracted with ether (1×100 mL, 3×75 mL)
- 10أخرىThe combined ether extracts were evaporated
- 11أخرىplaced in a 120° C.
- 12أخرى(ca. 15 minutes)
- 13درجة الحرارةThe mixture was cooled to room temperature
- 14workup.ADDITIONneutralized by addition of saturated NaHCO3 solution (150 mL)
- 15استخلاصthe resulting mixture extracted with CH2Cl2 (4×75 mL)
- 16تجفيفThe combined CH2Cl2 solution was dried (MgSO4)
- 17ترشيحfiltered
- 18أخرىevaporated
الإجراء التجريبي
Synthesized according to Agosta and Smith, J. Org. Chem. 35: 3856 (1970) A mixture of 2-methyl-1,3-cyclopentanedione (10.025 g, 89.4 mmol, Aldrich), methyl iodide (6.0 mL, 96.4 mmol, Aldrich), and KOH (5.097 g, 90.8 mmol) in water (25 mL)/dioxane (75 mL) was heated at reflux. After 5 hours, a solution of KOH (2 g) and MeI (2.4 mL) in water (5 mL)/dioxane (15 mL) was added and after another 3 hours at reflux, the solution was stirred at room temperature overnight. A solution of KOH (2 g) and MeI (2.4 mL) in water (5 mL)/dioxane (15 mL) was added to the overnight reaction and heating at reflux. After 4 hours, the mixture was cooled to room temperature and extracted with ether (1×100 mL, 3×75 mL). The combined ether extracts were evaporated, the residue combined with 10% HCl (50 mL), and the resulting mixture placed in a 120° C. oil bath until it began boiling (ca. 15 minutes). The mixture was cooled to room temperature, neutralized by addition of saturated NaHCO3 solution (150 mL) and the resulting mixture extracted with CH2Cl2 (4×75 mL). The combined CH2Cl2 solution was dried (MgSO4), filtered and evaporated to leave a brown oil (10.474 g, 83 mmol, 93%) which was used directly in the next step.