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

Temperature

100 °C

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]+.

1. filtrationThe reaction mixture was filtered
2. washthe solid material washed with DMF
3. customthe organic filtrate evaporated to dryness under reduced pressure
4. customThe crude reaction mixture
5. extractionextracted with dichloromethane (3×50 mL)
6. washthe combined organic phases washed with a sat. solution of sodium chloride (1×20 ml)
7. dry with materialdried over Na2SO4 providing 0.30 g (75%) of the title compound in sufficient purity for the next reaction step

ORD record

ord-dbae349b06c149359cfb99777320ce6a

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07645753B2