Boron trifluoride etherate → HCID 12134925, compound

Participants

Reaction Steps

2-Phenoxy-3-(4-benzyloxyphenyl)-3-hydroxy-2-methylpropionic acid ethyl ester (3.84 g, 9.5 mmol) in anhydrous CH2Cl2 (30 mL) was cooled to 0° C. and treated with BF3-Et2O (1.16 mL, 9.5 mmol) and triethylsilane (1.51 mL, 9.5 mmol). The mixture was stirred for 2 h and gradually warmed to ambient temperature. Saturated aqueous Na2CO3 (15 mL) was added and the mixture was stirred vigorously. The solution was partitioned and the organic layer was washed twice with water and brine, dried over Na2SO4, and concentrated in vacuo to produce 2-phenoxy-3-(4-benzyloxyphenyl)-2-methyl-propionic acid ethyl ester, shown above, as a colorless oil (1.34 g, 36%). Rf=0.90 (9:1 hexanes:ethyl acetate). 1H NMR (300 MHz, CDCl3): δ 7.36-7.42 (m, 3H), 7.34 (t, 1H), 7.17-7.24 (m, 5H), 6.98 (t, 1H), 6.91 (d, 2H), 6.83 (d, 2H), 5.05 (s, 2H), 4.22 (q, 1H, J=7.1), 3.26 (d, 1H, J=13.7), 3.13 (d, 1H, J=13.7), 1.40 (s, 3H), 1.22 (t, 3H, J=7.1). MS [EI+] 408 (M+NH4)+.

Provenance & Evidence