반응 #42372

반응 방정식

oxazole

n-butyl lithium

methyl 4-iodobenzoate

→

title compound

Methyl 4-(1,3-oxazol-2-yl)benzoate

용매

tetrahydrofuran

—

hexanes

diethyl ether

반응 조건

후처리

1. 1
   온도The reaction mixture is heated at 70° C. for 20 h under argon
2. 2
   온도cooled to room temperature
3. 3
   기타partitioned between ethyl acetate and water
4. 4
   세척The organic layer is washed with water and brine
5. 5
   건조dried (sodium sulfate)
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타Purification by flash column chromatography (3:1 hexanes/ethyl acetate)

실험 절차

To a −70° C., stirred solution of oxazole (190 μL, 3.8 mmol) in tetrahydrofuran (10 mL) is added n-butyl lithium (2.6 mL of a 1.6 M solution in hexanes, 4.2 mmol). After 30 min, zinc chloride (11.5 mL of a 1.0 M solution in diethyl ether, 11.5 mmol) is added. The reaction mixture is warmed to 0° C. and methyl 4-iodobenzoate (1 g, 3.8 mmol) and palladium(0)tetrakis(triphenylphosphine) (530 mg, 0.4 mmol) are added. The reaction mixture is heated at 70° C. for 20 h under argon, cooled to room temperature, and then partitioned between ethyl acetate and water. The organic layer is washed with water and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (3:1 hexanes/ethyl acetate) yields the title compound. 1H NMR (300 MHz, CDCl3) δ 8.14 (s, 4H), 8.07-8.05 (m, 1H), 7.36-7.35 (m, 1H), 3.95 (s, 3H).

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