Imidazole → HCID 57890161, compound

Participants

Reaction Steps

To a mixture of 5-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-carboxylic acid methyl ester (Example 2) (1.15 g, 2.66 mmol), imidazole (0.27 g, 4.00 mmol), and DMF (15 mL) is added TBSCl (0.54 g, 2.80 mmol). The reaction is stirred for 24 h. The reaction is diluted with Et2O (120 mL) and washed with 0.1 M HCl (3×40 ml). The organic layer is MgSO4 dried and concentrated. The resulting residue is chromatographed to give the title compound (0.94 g, 64%). 1H NMR (CDCl3), δ 0.01 (s, 3H), 0.06 (s, 3H), 0.65 (t, J=7.4 Hz, 6H), 0.85 (s, 9H), 0.91 (s, 9H), 2.00-2.14 (m, 4H), 2.14 (s, 3H), 2.43 (s, 3H), 3.67 (dd, J=5.8, 3.4 Hz, 1H), 3.74 (s, 3H), 3.85 (dd, J=9.8, 5.8 Hz, 1H), 3.98 (dd, J=9.8, 3.4 Hz, 1H), 6.56 (s, 1H), 6.68 (d, J=8.3 Hz, 1H), 6.96-7.03 (m, 2H). LC/MS (m/z): calcd for C31H51O4SSi (M+H)+: 547.9; found: 547.2.

Provenance & Evidence