tert-Butyl 2-(2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate → (E)-Methyl 5-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pent-2-enoate

Participants

Reaction Steps

(E)-Methyl 5-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pent-2-enoate was prepared using a procedure analogous to tert-butyl 2-(2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate except that tert-butyl 2-(2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate was replaced with (E)-methyl 5-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pent-2-enoate. The title compound was obtained (210 mg, 0.66 mmol, 89% yield) as a white solid. LCMS, [M−H]+=315.2. 1H NMR (500 MHz, CDCl3) δ 7.17 (t, J=8.0 Hz, 1H), 7.03-6.89 (m, 3H), 6.70 (ddd, J=8.0, 2.5, 1.0 Hz, 1H), 5.87 (dt, J=15.7, 1.5 Hz, 1H), 5.71 (s, 1H), 3.85 (s, 2H), 3.76 (s, 3H), 2.23-2.15 (m, 2H), 2.03 (dd, J=9.1, 4.7 Hz, 4H), 1.74-1.62 (m, 4H), 1.37-1.30 (m, 2H).

Provenance & Evidence