Hydrochloric Acid → Methyl 3-(4-((2-(2-(tosyloxy)ethyl)phenyl)ethynyl)phenyl)propanoate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence