反应详情

温度

10 °C

Methyl 3-(4-((2-(2-hydroxyethyl)phenyl)ethynyl)phenyl)propanoate (200 mg, 0.65 mmol) in CH2Cl2 (5 ml) was added para-toluenesulfonyl chloride (136 mg, 0.71 mmol). The mixture was cooled to 10° C. and NEt3 (72 mg, 0.71 mmol) in CH2Cl2 (1 ml) was added dropwise. The reaction was allowed to reach room temperature and reacted overnight. The reaction was added 1 M HCl (0.5 ml), water (10 ml) and extracted with CH2Cl2. The organic phases were combined, washed with aq. NaHCO3, dried over MgSO4, concentrated and purified by flash chromatography (SiO2, EtOAc:PE, 1:3) to give 153 mg (51%): Rf=0.20 (EtOAc:PE, 1:3); 1HNMR (CDCl3): δ 7.66 (d, J=6.3 Hz, 2H), 7.44-7.42 (m, 1H), 7.39 (d, J=6.3 Hz, 2H), 7.26-7.23 (m, 1H), 7.22-7.19 (m, 6H), 4.32 (t, J=5.1 Hz, 2H), 3.68 (s, 3H), 3.21 (t, J=5.7 Hz, 2H), 2.98 (t, J=6.0 Hz, 2H), 2.65 (t, J=5.4 Hz, 2H), 2.38 (s, 3H); 13CNMR (CDCl3): δ 173.1, 144.5, 141.2, 137.8, 133.0, 132.3, 131.7, 129.9, 129.7, 128.5, 128.5, 127.8, 127.0, 123.1, 120.9, 93.6, 86.8, 51.7, 35.4, 34.4, 30.9, 21.6.

1. customto reach room temperature
2. customreacted overnight
3. extractionextracted with CH2Cl2
4. washwashed with aq. NaHCO3
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. custompurified by flash chromatography (SiO2, EtOAc:PE, 1:3)
8. customto give 153 mg (51%)