Tetrahydrofuran → (S)-ethyl 2-tert-butoxy-2-(6-formyl-3-methyl-1-(trifluoromethyl-sulfonyloxy)naphthalen-2-yl)acetate

Participants

Reaction Steps

A solution of (S)-ethyl 2-tert-butoxy-2-(3-methyl-1-(trifluoromethylsulfonyloxy)-6-vinylnaphthalen-2-yl)acetate (0.60 g, 1.3 mmol) in THF (7 mL) at room temperaturewas treated with a previously prepared mixture of K2OsO4.2H2O (0.023 g, 0.063 mmol) and NaIO4 (0.81 g, 3.8 mmol) in water (5 mL). The resulting suspension becomes thick and opaque. After vigorous stirring for 20 min, the suspension is filtered through a pad of Celite, and the filtrate is washed with batches of EtOAc until white in color. The collected mother liquor is further diluted with water and EtOAc. Following separation, the aqueous layer is extracted with EtOAc until colorless. The combined organics are washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue is purified by Yamazen column chromatography (15-35% EtOAc/hex) to afford the desired material. 1H-NMR: 400 MHz, (CDCl3) δ: 10.19 (s, 1H); 8.31 (br s, 1H); 8.16 (d, J=8.8 Hz, 1H); 8.05 (dd, J=8.8, 1.6 Hz, 1H); 7.85 (s, 1H); 5.76 (s, 1H); 4.28-4.10 (m, 2H); 2.61 (s, 3H); 1.22 (s, 9H); 1.18 (t, J=7.2 Hz, 3H).

Provenance & Evidence