反应详情

Oxalyl chloride (132 μL, 1.5 mmol) was added over a 10 minute period to a mixture of 3-phenylbenzoic acid (200 mg, 1 mmol) dissolved in a mixture THF/DMF (3.5 mL/58 μL). After the addition, the reaction was stirred at room temperature for 2.5 hours. n-Butylamine (247 μL, 2.5 mmol) was then added into half of the acid chloride solution at 0° C. The reaction was then stirred at room temperature for 18 hours. The reaction was concentrated and water was added to the residue. The aqueous phase was extracted 3 times with CH2Cl2. The combined organic layers were washed with 2N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. Diethyl ether was added to the residue and a white solid precipitated. It was collected by filtration and rinsed with a small amount of diethyl ether. The white solid was then dried under vacuum (88 mg, 70%). NMR 1H (ppm, CDCl3): 7.96 (s, 1H), 7.69 (d, J3=8.01 Hz, 2H), 7.59 (d, J3=7.16 Hz, 2H), 7.51-7.34 (m, 4H), 6.11 (br. s., 1H), 3.51-3.44 (m, 2H), 1.64 (sext., J3=7.59 Hz, 2H), 1.43 (quint., J3=7.98 Hz, 2H), 0.96 (t, J3=7.32 Hz, 3H).

1. additionAfter the addition
2. stirringThe reaction was then stirred at room temperature for 18 hours
3. concentrationThe reaction was concentrated
4. additionwater was added to the residue
5. extractionThe aqueous phase was extracted 3 times with CH2Cl2
6. washThe combined organic layers were washed with 2N HCl, saturated NaHCO3, brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. additionDiethyl ether was added to the residue
10. customa white solid precipitated
11. filtrationIt was collected by filtration
12. washrinsed with a small amount of diethyl ether
13. customThe white solid was then dried under vacuum (88 mg, 70%)