Toluene → 2-(3,5-Diallyloxy-2-ethylphenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

Methyl 3,5-diallyloxy-2-ethylphenylacetate (0.84 g, 2.9 mmol) obtained in Example 5, Step 3 was dissolved in dichloromethane (15 mL). After the solution was cooled to −78° C. in an atmosphere of nitrogen, a 1.0 mol/L solution of diisobutylaluminum hydride in toluene (8.4 mL, 8.4 mmol) was added dropwise thereto, followed by stirring at −78° C. for 4 hours. To the reaction mixture was added a saturated aqueous solution of potassium sodium tartrate (50 mL), and the mixture was stirred at room temperature for 3 hours and then extracted with ethyl acetate (0.10 L×2). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/1) to obtain 2-(3,5-diallyloxy-2-ethylphenyl)ethanol (0.74 g, 97%). 1H-NMR (CDCl3, 270 MHz) δ (ppm): 6.37 (brs, 2H), 6.11-5.98 (m, 2H), 5.47-5.35 (m, 2H), 5.30-5.23 (m, 2H), 4.52-4.49 (m, 4H), 3.82 (q, J=6.8 Hz, 2H), 2.88 (t, J=6.8 Hz, 2H), 2.64 (q, J=7.4 Hz, 2H), 1.10 (t, J=7.4 Hz, 3H)

Provenance & Evidence