Tin tetrachloride → [2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl4-methoxy-phenyl)-methanone

Participants

Reaction Steps

The title compound was prepared according to the procedure in Example 5, step 2 using 3-cyclopentyl-p-anisic acid (2.00 g, 9.08 mmol, RN-59216-82-9), oxalyl chloride (0.871 mL, 9.99 mmol), N,N-dimethylformamide (2 drops), tin (IV) chloride (1.17 mL, 4.58 mmol) and 2-(2-bromo-benzyl)-4,5-dimethyl-furan (2.41 g, 9.08 mmol) in CH2Cl2. Purification on Biotage KP-Sil eluting with 4% EtOAc/pet. ether gave 2.82 g (66%) of the title compound as a clear oil. 1H NMR (DMSO-d6) δ1.40-1.44 (m, 2 H), 1.57-1.73 (m, 4 H), 1.79 (s, 3 H), 1.87-1.93 (m, 2 H), 2.16 (s, 3 H), 3.21 (quintet, 1 H), 3.86 (s, 3 H),3.93 (s, 2 H), 7.04 (d, 1 H), 7.11-7.18 (m, 2 H), 7.29 (t, 1 H), 7.51 (dd, 1 H), 7.54-7.60 (m, 2 H).

Provenance & Evidence