Selectfluor → (S)-ethyl 2-tert-butoxy-2-(4-fluoro-1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate
Reaktionsgleichung
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]=1[OH:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)[F:26].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[C:20]([F:26])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]=1[OH:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]Komponenten
4
Versuchsvorschrift
A solution of (S)-ethyl 2-tert-butoxy-2-(1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate (0.62 g, 1.9 mmol) in MeCN (14 mL) cooled to 0° C. was treated with SelectFluor® fluorinating reagent (0.66 g, 1.9 mmol). The cold bath was removed and after 90 minutes the reaction was quenched with pH 7 buffer solution. The aqueous layer was extracted with EtOAc and the combined organics washed with brine and dried over anhydrous MgSO4 and filtered. Following concentration in vacuo, the desired product was obtained via silica gel chromatography followed by preparatory HPLC to afford (S)-ethyl 2-tert-butoxy-2-(4-fluoro-1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate. LCMS-ESI− (m/z): [M−H]− calcd for C20H24O4F: 347.4. found: 347.2.