Boron trifluoride etherate → 2-Phenoxy-3-(4-benzyloxynaphthalen-1-yl)-2-methylpropionic acid ethyl ester

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Reaction Steps

3-(4Benzyloxynaphthalen-1-yl)-2-phenoxy-3-hydroxy-2-methylpropionic acid ethyl ester (1.80 g, 3.9 mmol) in anhydrous CH2Cl2 (20 mL) was cooled to 0° C. and treated with BF3-Et2O (0.48 mL, 3.9 mmol, d=1.154) and triethylsilane (0.63 mL, 3.9 mmol, d=0.728). The mixture was stirred for 2 hr, gradually warming to ambient temperature. Saturated aqueous Na2CO3 (15 mL) was added and the mixture was stirred vigorously for 15 min. The solution was partitioned and the organic layer was washed twice with water and brine, dried over Na2SO4, and concentrated in vacuo to 3-(4-benzyloxynaphthalen-1-yl)-2-phenoxy-2-methylpropionic acid ethyl ester as a golden oil (1.55 g, 89%). Rf=0.41 (9:1 hexanes:ethyl acetate). 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J=8.3), 8.11 (d, 1H, J=8.3), 7.47 (d, 2H, J=7.8), 7.40 (t, 1H, J=8.3), 7.37 (t, 1H, J=8.3), 7.36 (t, 2H, J=7.8) 7.28 (d, 2H, J=7.8), 7.11 (t, 2H, J=8.8), 6.87 (t, 1H, J=7.8), 6.79 (d, 1H, J=7.8), 6.69 (d, 2H, J=8.8), 5.18 (s, 2H, 4.08 (q, 2H, J=7.0), 3.66 (d, 1H, J=14.4), 3.54 (d, 1H, J=14.4), 1.38 (s, 3H), 1.13 (t, 3H, J=7.0). MS [EI+] 458 (M+NH4)+

Provenance & Evidence