Tin tetrachloride → [2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-methoxy-phenyl)-methanone

Participants

Reaction Steps

The title compound was prepared according to the procedure in Example 5, step 2 using 3,5-diisopropyl-p-anisic acid (0.983 g, 4.16 mmol, RN-117439-59-5), oxalyl chloride (0.398 mL, 4.56 mmol), N,N-dimethylformamide (2 drops), tin (IV) chloride (0.535 mL, 4.58 mmol) and 2-(2-bromo-benzyl)4,5-dimethyl-furan (1.10 g, 4.16 mmol) in CH2Cl2. Purification on Biotage KP-Sil eluting with 3% EtOAc/pet. ether gave 0.990 g (49%) of the title compound as a clear oil. 1H NMR (DMSO-d6) δ1.15 (d, 12 H), 1.84 (s, 3 H), 2.18 (s, 3 H), 3.27 (septet, 2 H), 3.73 (s, 3 H), 3.91 (s, 2 H), 7.12-7.16 (m, 2 H), 7.29 (t, 1 H, 7.44 (s, 2 H), 7.50 (d, 1 H).

Provenance & Evidence