Oxalyl chloride → HCID 23445655, compound

Participants

Reaction Steps

The title compound was prepared according to the procedure in Example 5, step 2 using 3-cyclopentyl-p-anisic acid (5.0 g, 22.7 mmol, RN-59216-82-9), oxalyl chloride (2.4 mL, 27.2 mmol), N,N-dimethylformarnide (2 drops) tin(IV) chloride (2.9 mL, 25.0 mmol) and 2-benzyl-2,3-dimethylthiophene (5.1 g, 25.0 mmol). Purification on silica gel eluting 5% EtOAc/pet. ether gave 4.8 g (52%) of the title compound as an amber oil. (DMSO-d6) δ 7.61-7.54 (m, 2 H), 7.24-7.14 (m, 3 H), 7.08-7.02 (m, 3 H), 3.87 (s, 3 H), 3.84 (s, 2 H), 3.42-3.30 (m, 1 H), 2.26 (s, 3 H), 2.00-1.85 (m, 2 H), 1.81 (s, 3 H), 1.74-1.58 (m, 4 H), 1.48-1.36 (m, 2 H). mass spectrum (EI) m/z 404 (M+). Anal. Calc. for C26H28O2S: C, 77.19, H, 6.98, N, 0.00. Found: C, 76.26, H, 7.24, N, 0.04.

Provenance & Evidence