Isopropanol → HCID 69202506, compound

Temperature

-78 °C

A stirred mixture of 4-bromo-2-ethoxy-1-methoxy-benzene (1.71 g, 7.4 mmol) and dry THF (18 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (3.0 mL, 7.4 mmol) and stirred for 20 min. Then a mixture of 4-dimethylamino-benzaldehyde (1.00 g, 6.7 mmol) in dry THF (10 mL) was added and stirred for 2 hour at −78° C. The mixture was quenched with isopropanol (3.1 mL, 40 mmol) and added water (10 mL). The mixture was extracted with EtOAc (3×50 mL). The combined organic phases were washed with water (2×50 mL), dried over MgSO4 and concentrated to oil, which was purified by flash column chromatography (EtOAc/Hexane) to give (4-dimethylamino-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanol as an off-white solid (1.29 g, 64% yield): 1H NMR (CDCl3) δ 1.44 (t, J=7 Hz, 3H, CH2CH3), 2.04 (d, J=3 Hz, 1H, OH), 2.93 (s, 6H, N(CH3)2), 3.85 (s, 3H, OCH3), 4.07 (q, J=7 Hz, 2H, CH2CH3), 5.72 (d, J=3 Hz, 1H, CH), 6.68-7.23 (m, 7H, Ar). The product was used in the next step without further purification.

1. customevacuated
2. additionrefilled with nitrogen for 10 cycles
3. additionwas added
4. stirringstirred for 2 hour at −78° C
5. extractionThe mixture was extracted with EtOAc (3×50 mL)
6. washThe combined organic phases were washed with water (2×50 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated to oil, which
9. customwas purified by flash column chromatography (EtOAc/Hexane)

ORD record

ord-a779507e72284a1eb7781975f745bc50

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470723B2