HCID 58675134, compound → 3-Hydroxy-5-(4-iodo-phenyl)-pentanoic acid

Participants

Reaction Steps

Silica gel (19 g) was added to a stirred solution of 3-hydroxy-5-(4-iodo-phenyl)-pentanoic acid tert-butyl ester (Intermediate 9, 1.2 g, 3.2 mmol) in toluene (100 mL) and the resulting suspension heated at reflux for 5.5 hours. The reaction was cooled to room temperature and then filtered through a thin pad of celite, washing with 20% methanol/dichloromethane (2×50 mL). The filtrate was evaporated under reduced pressure to give the title compound (586mg, 57%) as a white solid. LC/MS: 3.01 min; z/e 319, calcd (M−1) 319. 1H NMR (400 MHz: DMSO-d6): 7.63 (2 H), 7.00 (2 H), 3.77 (1 H), 2.60 (2 H), 2.3 (2 H), 1.62 (2 H).

Provenance & Evidence