反应 #2487458

反应方程式

N-methoxy-N-methylbenzamide

tert-butyl (4-cyclopropyl-2-methylphenyl)carbamate

sec-butyllithium

→

title compound

收率 59.5%

tert-Butyl[4-cyclopropyl-2-(2-oxo-2-phenylethyl)phenyl]carbamate

收率 59.5%

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred at −45° C. for 35 minutes
2. 2
   workup.STIRRINGstirred at room temperature for 2 more hours
3. 3
   其他The reaction mixture was quenched with saturated aqueous ammonium chloride solution/water (2/1, 30 mL)
4. 4
   萃取followed by extraction with ethyl acetate
5. 5
   洗涤The organic layer was washed with saturated brine
6. 6
   干燥dried over anhydrous sodium sulfate
7. 7
   浓缩concentrated under reduced pressure
8. 8
   其他The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

Under an argon atmosphere, to a solution of tert-butyl (4-cyclopropyl-2-methylphenyl)carbamate (666 mg) in tetrahydrofuran (13.5 mL) was added dropwise sec-butyllithium (1.08 mol/L hexane-cyclohexane solution, 5.5 mL) at −45° C., and the mixture was stirred for 30 minutes. Next, a solution of N-methoxy-N-methylbenzamide (489 mg) in tetrahydrofuran (1.4 mL) was added dropwise thereto, and the mixture was stirred at −45° C. for 35 minutes and then stirred at room temperature for 2 more hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution/water (2/1, 30 mL), followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (563 mg). 1H-NMR (CDCl3) δ ppm: 0.55-0.70 (2H, m), 0.80-1.00 (2H, m), 1.49 (9H, s), 1.75-1.90 (1H, m), 4.25 (2H, s), 6.85-7.00 (2H, m), 7.20-7.75 (5H, m), 8.00-8.15 (2H, m).

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