반응 #521023

반응 방정식

4-bromobutyrylferrocene

potassium iodide

triethylamine

→

desired compound

수율 15.0%

Ferrocene

수율 15.0%

용매

toluene

반응 조건

후처리

1. 1
   온도The reaction mixture was refluxed overnight
2. 2
   기타Upon completion of reaction (as shown by TLC)
3. 3
   workup.ADDITIONSilica gel (1 g) was added
4. 4
   기타the solvent was evaporated
5. 5
   세척eluted with 5% methanol in methylene chloride

실험 절차

To a solution of N-(9-azabicyclo[3.3.1] nonan-3a-yl)-N′-(2-methoxy-5-methylphenyl) carbamate (350 mg, 1.15 mmol) in toluene (10 mL) was added 4-bromobutyrylferrocene (385 mg, 1.15 mmol), potassium iodide (166 mg, 1.00 mmol), and triethylamine (500 mg, 4.94 mmol). The reaction mixture was refluxed overnight. Upon completion of reaction (as shown by TLC), the mixture was cooled to room temperature. Silica gel (1 g) was added, and the solvent was evaporated. The resulting solid was layered onto a silica gel column and eluted with 5% methanol in methylene chloride. The desired compound was isolated in 15 % yield (100 mg): mp 94-95° C.; 1H NMR (300 MHz, CDCl3) δ 7.89 (s, 1H), 7.13 (s, 1H), 6.75-6.84 (m, 2H), 5.19-5.21 (m, 1H), 4.80 (s, 2H), 4.56 (s, 2H), 4.21 (s, 5H), 3.92 (s, 3H), 3.65 (s, 2H), 3.16-3.24 (m, 2H), 2.90-2.98 (m, 4H), 2.40-2.52 (m, 3H), 2.31 (s, 3H), 2.00-2.06 (m, 3H), 1.70-1.78 (m, 4H).

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