[CH3:1][C:2]([SH:5])([CH3:4])[CH3:3].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9](F)[C:8]=1[C:14]1[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=1.[H-].[Na+]>C1COCC1>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:5][C:2]([CH3:4])([CH3:3])[CH3:1])[C:8]=1[C:14]1[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=1A 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 1d, then at reflux for 1d. 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.
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