反応 #2471708

反応方程式

triethylamine

p-Toluene sulfonyl chloride

N-(1-hydroxy-2-methylpropan-2-yl)quinoline-2-carboxamide

→

4,4-dimethyl-2-(quinoline-2-yl)-oxazoline

収率 47.0%

溶媒

DCM

DCE

DCE

反応条件

後処理

1. 1
   その他To an oven dried 250 mL round bottomed flask
2. 2
   workup.ADDITIONA magnetic stirbar was added
3. 3
   workup.ADDITIONadded to the flask dropwise via syringe
4. 4
   その他was fitted to the flask
5. 5
   温度heated
6. 6
   温度to reflux for 16 h
7. 7
   温度The reaction mixture was cooled to room temperature
8. 8
   その他transferred to a separatory funnel
9. 9
   洗浄The organic phase was washed with saturated NaHCO3 solution (2×70 mL), H2O (2×70 mL), and Brine (1×70 mL)
10. 10
    乾燥Dried over Na2SO4
11. 11
    ろ過filtered
12. 12
    濃縮concentrated under reduced pressure
13. 13
    その他The crude mixture was purified by flash chromatography
14. 14
    洗浄eluting with 20%→30% acetone in hexanes

実験手順

To an oven dried 250 mL round bottomed flask was weighed p-Toluene sulfonyl chloride (1.049 g, 5.5 mmol) and N,N-dimethylaminopyridine (39.1 mg, 0.32 mmol). A magnetic stirbar was added and the flask was placed under N2 atmosphere. The flask was charged with DCE (20 mL) and triethylamine (3.2 mL, 23 mmol). The N-(1-hydroxy-2-methylpropan-2-yl)quinoline-2-carboxamide (1.112 g, 4.55 mmol) was dissolved in DCE (15 mL) and added to the flask dropwise via syringe. The reaction mixture was stirred at 0° C. for 15 min, before a reflux condenser was fitted to the flask and heated to reflux for 16 h. The reaction mixture was cooled to room temperature, transferred to a separatory funnel and diluted with DCM (70 mL). The organic phase was washed with saturated NaHCO3 solution (2×70 mL), H2O (2×70 mL), and Brine (1×70 mL). Dried over Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was purified by flash chromatography eluting with 20%→30% acetone in hexanes to afford 4,4-dimethyl-2-(quinoline-2-yl)-oxazoline in 47% yield (484 mg, 2.14 mmol) according to the reaction

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