tert-Butyl mercaptan → 2-[2-Fluoro-6-(1,1-dimethylethylthio)phenyl]-4,4-dimethyl-2-oxazoline

Participants

Reaction Steps

A mixture of 2-methyl-2-propanethiol (2.7 g, 30 mmol), the compound of example g (3.17 g, 15 mmol), and NaH (0.79 g, 33 mmol) in THF (100 mL) was stirred at RT for 1 d, then at reflux for 1 d. This was then quenched with sat aq NaHCO3 (50 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 1:4 EtOAc/hexanes to afford 3.5 g of 2-[2-fluoro-6-(1,1-dimethylethylthio)phenyl]-4,4-dimethyl-2-oxazoline as a yellow oil, an 83% yield.

Provenance & Evidence