Isopropanol → HCID 69203609, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 4-bromo-2-ethoxy-1-methoxy-benzene (5.25 g, 22.7 mmol) and dry THF (50 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (9.1 mL, 22.7 mmol) and stirred for 20 min. Then a mixture of 3-benzyloxy-4-methoxy-benzaldehyde (5.0 g, 20.6 mmol) in dry THF (20 mL) was added and stirred for 1 hour at −78° C. The mixture was quenched with isopropanol (9.4 mL, 248 mmol) and added water (50 mL). The mixture was extracted with EtOAc (3×80 mL). The combined organic phases were washed with water (2×80 mL), dried over MgSO4 and concentrated to oil, which was purified by flash column chromatography (EtOAc/Hexane) to give (3-benzyloxy-4-methoxy-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanol as an off-white solid (7.26 g, 89% yield): 1H NMR (CDCl3) 1.43 (t, J=7 Hz, 3H, CH2CH3), 2.09 (d, J=3 Hz, 1H, OH), 3.86 (s, 3H, OCH3), 3.87 (s, 3H, OCH3), 4.00 (q, J=7 Hz, 2H, CH2CH3), 5.10 (s, 2H, CH2), 5.68 (d, J=3 Hz, 1H, CH), 6.80-6.92 (m, 6H, Ar), 7.26-7.41 (m, 5H, Ar). The product was used in the next step without further purification.

Provenance & Evidence