Methanol → 7-[4-({[3-[2-(2,6-Dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 7-[4-({[3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylate (0.052 g, 0.09 mmol) in tetrahydrofuran (0.9 mL) was placed in a microwave reaction tube. Methanol (0.45 mL) was added followed by 1N sodium hydroxide (0.14 mL, 0.14 mmol). The tube was sealed and heated in a microwave reactor to 100° C. for 600 seconds. The solution was neutralized and concentrated. Water was added and the mixture was filtered. The resulting solid was dried in a vacuum oven at 45° C. with P2O5 to yield the title compound (0.039 g, 74% as 0.40 tetrahydrofuran) 1H NMR (DMSO-d6): 13.13 (s, 1H), 9.10 (s, 1H), 8.17-8.15 (m, 1H), 8.07 (d, J=9 Hz, 1H) 7.87 (dd, J=2, 9 Hz; 1H), 7.71 (d, J=9 Hz, 2H), 7.57-7.54 (m, 1H), 7.41 (d, J=8 Hz, 2H), 7.28-7.24 (m, J=8 Hz, 2H), 7.16 (dd, J=9, 2 Hz, 2H), 4.98 (s, 2H), 3.36 (septet, overlapping H2O, 1H), 3.23-3.20 (m, 2H), 2.89-2.85 (m, 2H), 1.25 (d, J=7 Hz, 6H). HRMS C32H27NO4Cl2 m/z 560.1395 (M+H)+Cal; 560.1375 (M+H)+Obs.

Provenance & Evidence