Tin tetrachloride → (2-Naphthalen-2-ylmethyl-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 (0.93 g, 3.95 mmol, RN-1 17439-59-5), oxalyl chloride (0.377 mL, 4.33 mmol), N,N-dimethylformamide (2 drops), tin (IV) chloride (0.507 mL, 4.33 mmol) and 2-naphthalen-2-ylmethyl-4,5-dimethylfuran (0.93 g, 3.94 mmol) in CH2Cl2. Purification on Biotage KP-Sil eluting with a 2 & 4% EtOAc/pet. ether step gradient gave 0.357 g (20%) of the title compound. 1H NMR (DMSO-d6) δ 1.14 (d, 12H), 1.82 (s, 3H), 2.20 (s, 3H), 3.27 (septet, 2H), 3.74 (s, 3H), 4.02 (s, 2H), 7.19 (dd, 1H), 7.45-7.52 (m, 5H), 7.76-7.79 (m, 3H).

Provenance & Evidence