4-Benzyloxy-2-phenoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester → 4-Hydroxy-2-phenoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester

Participants

Reaction Steps

10% Pd on Carbon (50 mg) was added to a solution of 4-benzyloxy-2-phenoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester (214a) (500 mg, 1.16 mmol) in EtOAc (10 mL). The mixture was stirred under H2 balloon for 3 days. The mixture was filtered through Celite and concentrated to give a colorless oil (400 mg, 88% yield). 1H NMR (400 MHz, CDCl3) δ 7.22-7.32 (m, 2 H) 7.18 (s, 1 H) 7.04 (s, 1 H) 6.91-6.95 (m, 2 H) 6.85 (d, J=7.58 Hz, 1 H) 5.18-5.28 (m, 1 H) 4.09-4.17 (m, 2 H) 3.38 (dd, J=16.17, 9.60 Hz, 1 H) 3.15 (dd, J=16.29, 6.69 Hz, 1 H) 1.58 (s, 9 H); LCMS for C20H22O5 m/z 365.00 (M+Na)+.

Provenance & Evidence