Sodium Carbonate → HCID 86691562, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 2-(4-fluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate (1.08 g, 2.64 mmol) in PhMe (20 mL) was cooled to −40° C. (dry ice/CH3CN bath). (R) —CBS catalyst (146 mg, 0.528 mmol) was introduced. Distilled catecholborane (423 μL) was added dropwise over a 5 min period. After 30 min, the reaction was warmed to −20° C. and treated with EtOAc (20 mL). Then 15% Na2CO3 (10 mL) was added. The reaction was warmed to 23° C. and stirred vigorously. The organic phase was collected after 30 min. It was washed (vigorous stirring) with 10 mL portions of 15% Na2CO3 for 30 min each until the layer was colorless. (Early washes tended to be dark greenish-brown). After six such washings, the organic phase was treated with saturated NH4Cl (20 mL) for 30 min. The organic phase was dried (MgSO4), filtered, and concentrated. The residue was treated with hexanes and concentrated again. The material was dissolved in benzene. The solution was wet-loaded onto a 40 g “gold” ISCO silica gel column and purified by flash chromatography (hexane→ethyl acetate) giving the desired product (1.02 g, 94% yield). 1H NMR (400 MHz, CDCl3) δ 8.11-8.06 (m, 2H), 7.67-7.64 (m, 2H), 5.79 (s, 1H), 4.33-4.22 (m, 2H), 2.40 (d, JHF=3.2 Hz, 3H), 1.22 (t, J=7.4 Hz, 3H). 19F NMR (377 MHz, CDCl3) δ−122.6 (app. s, 1F), −73.1 (s, 3F).

Provenance & Evidence