反应详情

To a dried Schlenk flask filled with nitrogen was added Pd(PPh3)4 (56.5 mg, 0.049 mmol), CuI (14.2 mg, 0.075 mmol), ethyl 2-(4-ethynylphenoxy)acetate (150.0 mg, 0.734 mmol), and 4-iodophenol (195.3 mg, 0.888 mmol) was added. The flask was evacuated, equipped with a septum, and filled with nitrogen. DMF (10 mL) and DIPEA (0.26 mL, 1.5 mmol) were added through the septum. The reaction was stirred for 3 days and was neutralized with saturated aqueous NH4Cl (5 mL). Water (5 mL) was added and the mixture was extracted with EtOAc (3×10 mL). The combined EtOAc phases was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The product was purified with dry column vacuum chromatography (EtOAc:hexanes 1:90→90:1 v/v). The final product was white and solid (129.6 mg, 60%) Rf=0.48 (EtOAc:hexanes 1:1 v/v). 1H-NMR (DMSO-d6): □ 1.21 (t, 3H, J=7.2 Hz, CH2CH3); 4.17 (q, 2H, J=7.1 Hz, CH2CH3); 4.82 (s, 2H, OCH2); 6.78 (d, 2H, J=8.7 Hz, Ph); 6.95 (d, 2H, J=9.0 Hz, Ph); 7.34 (d, 2H, J=8.7 Hz, Ph); 7.43 (d, 2H, J=8.7 Hz, Ph); 9.67 (s, 1H, OH). 13C-NMR (DMSO-d6): □ 14.0 (CH2CH3); 60.7 (CH2CH3); 64.7 (OCH2); 87.1 (CC); 88.6 (CC); 112.8, 114.9, 115.6, 115.7, 132.6, 132.8, 157.5, 157.8 (Ph); 168.5 (COO). MALDI-MS: m/z calculated for C18H16O3 [M]+ 296.1043. found 296.1046.

1. additionTo a dried Schlenk flask filled with nitrogen
2. additionwas added
3. customThe flask was evacuated
4. customequipped with a septum
5. additionfilled with nitrogen
6. extractionthe mixture was extracted with EtOAc (3×10 mL)
7. washThe combined EtOAc phases was washed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated under reduced pressure
10. customThe product was purified
11. dry with materialwith dry column vacuum chromatography (EtOAc:hexanes 1:90→90:1 v/v)