Triethylamine → HCID 23590002, compound

Participants

Reaction Steps

2-(2-Phenyl-5-propyloxazol-4-yl)ethanol (225 mg, 0.97 mmol) and triethyl amine (167 mg, 1.65 mmol, 0.23 mL) were dissolved in CH2Cl2 (3.5 mL) at 0° C. and treated with methane sulfonyl chloride (167 mg, 1.46 mmol, 0.11 mL). After 1 h, NH4Cl (25 mL of a 10% aqueous solution) was added and then the organic phase was dried (MgSO4), filtered and concentrated to an oil. The intermediate mesylate was combined with Cs2CO3 (383 mg, 1.18 mmol), and 2-(4-hydroxyphenoxy)-2-methylpropanoic acid ethyl ester (American Home Products U.S. Pat. No. 3,795,691) (190 mg, 0.84 mmol) in DMF (4 mL) and heated to 55° C. After 18 h, the reaction mixture was partitioned between H2O (25 mL) and EtOAc (25 mL) and then the organic phase washed with H2O (2×), dried (MgSO4), filtered and concentrated. The product was purified by flash chromatography (70 mL SiO2, hexanes to 20% EtOAc/hexanes) and obtained as a colorless oil (170 mg, 46%): Rf=0.49 in 20% EtOAc/hexanes; 1H NMR (500 MHz, CDCl3) δ 8.00-7.96 (m, 2H), 7.42-7.38 (m, 3H), 6.83-6.76 (m, 4H), 4.22 (q, J=7.0 MHz, 2H), 4.19 (t, J=7.0 Hz, 2H), 2.95 (t, J=7.0 Hz, 2H), 2.67 (t, J=7.0 Hz, 2H) 1.71 (sextet, J=7.0 Hz, 2H), 1.52 (s, 6H), 1.26 (t, J=7.0 Hz, 3H), 0.96 (t, J=7.0 Hz, 3H).

Provenance & Evidence