Potassium Iodide → (3-Ethoxy-5-isobutoxy-phenyl)-methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-ethoxy-5-hydroxymethyl-phenol (0.3 g, 1.78 mmol, 1.0 equiv; prepared as described for intermediate 41 [3-ethoxy-5-(3-hydroxy-2-2-dimethylpropoxy)-benzaldehyde]) in DMF (2 mL) was added cesium carbonate (2.32 g, 7.14 mmol, 4.0 equiv), potassium iodide (0.59 g, 3.57 mmol, 2.0 equiv) and 1-bromo-2-methyl-propane (0.58 mL, 0.73 g, 5.35 mmol, 3.0 equiv) and the reaction mixture stirred under Ar at 100° C. for 24 h. The reaction mixture was filtered, the solid material washed with DMF and the organic filtrate evaporated to dryness under reduced pressure. The crude reaction mixture was suspended in water (20 mL), extracted with dichloromethane (3×50 mL), the combined organic phases washed with a sat. solution of sodium chloride (1×20 ml) and dried over Na2SO4 providing 0.30 g (75%) of the title compound in sufficient purity for the next reaction step. 1H NMR (300 MHz, CDCl3): δ 1.01 (d, J=6.7 Hz, 6H), 1.40 (t, J=7.0 Hz, 3H), 2.07 (h, J=6.7 Hz, 1H), 3.70 (d, J=6.7 Hz, 2H), 4.02 (q, J=7.0 Hz, 2H), 4.61 (br s, 2H), 6.37-6.39 (m, 1H), 6.49-6.51 (m, 2H). 13C NMR (75 MHz, CDCl3): δ 14.84, 19.26, 28.31, 63.56, 65.49, 74.62, 100.76, 105.14, 105.32, 143.29, 160.41, 160.78. MS (ISP): 225.1 [M+H]+.

Provenance & Evidence