反应详情

To a dried Schlenk flask filled with nitrogen was added Pd(PPh3)4 (17.3 mg, 0.015 mmol), CuI (6.6 mg, 0.035 mmol), ethyl 2-(4-ethynylphenoxy)acetate (60.6 mg, 0.294 mmol), and 3-iodophenol (78.4 mg, 0.352 mmol) was added. The flask was evacuated, equipped with a septum, and filled with nitrogen. DMF (5 mL) and DIPEA (0.1 mL, 0.6 mmol) were added through the septum. The reaction was stirred over night and was neutralized with saturated aqueous ammonium chloride (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 on a dry silica column (EtOAc:hexanes 1:90→90:1 v/v). The final product was yellow/orange and solid (52 mg, 60%). Rf=0.46 (EtOAc:hexanes 1:1 v/v). 1H-NMR (DMSO-d6): □ 1.22 (t, 3H, J=7.7 Hz, CH2CH3); 4.18 (q, 2H, J=7.5 Hz, CH2CH3); 4.84 (s, 2H, OCH2); 6.9 (m, 5H, Ph); 7.20 (t, 1H, J=8.0 Hz, Ph); 7.49 (m, 2H, Ph); 9.67 (s, 1H, OH). 13C-NMR (DMSO-d6): □ 14.0 (CH2CH3); 60.7 (CH2CH3); 64.7 (OCH2); 88.3 (CC); 88.6 (CC); 115.0, 116.0, 117.6, 122.1, 123.4, 128.4, 129.8, 132.9, 157.3, 157.8 (Ph); 168.5 (COO).

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 on a dry silica column (EtOAc:hexanes 1:90→90:1 v/v)