Nitrogen → 2-Methyl-2-phenoxy-3-thiophen-2-yl-propionic Acid Methyl Ester

Participants

Reaction Steps

In a 100 mL beaker, 1.12 g of 1-methyl-3-nitro-1-nitrosoguanidine (MNNG) was added to a solution of ether (30 mL) and 5 N KOH (2.3 mL) and stirred until N2 evolution ceased. In another beaker, crude 2-methyl-2-phenoxy-3-thiophen-2-yl-propionic acid (1.00 g) was dissolved in CH2Cl2 (20 mL). The beaker containing the ether/base mixture was then placed in a Dewar flask containing dry ice/acetone, the aqueous layer was frozen and the ether layer decanted into the other beaker containing the crude acid solution. This mixture was then stirred for an additional 5 min, which by HPLC showed the reaction to be complete. The solvent was removed in vacuo to provide a crude oil. Purification by flash chromatography EtOAc: hexane (1:10) provided 533 mg of desired product (28%): 1H NMR (400 MHz, CDCl3) • 7.16-7.22 (m, 4H), 6.96 (m, 1H), 6.91 (m, 1H), 6.84 (m, 2H), 3.73 (s, 3H), 3.49 (d, 1H), 3.38 (d, 1H), 1.42 (s, 3H); MS (EI) 277.1 (M+H)+.

Provenance & Evidence