Isopropanol → HCID 384224, compound

Temperature

-78 °C

A stirred mixture of 1-bromo-4-methoxy-benzene (1.79 g, 9.6 mmol) and dry THF (25 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (3.6 mL, 9.1 mmol) and stirred for 20 min. Then a mixture of benzo[1,3]dioxole-5-carbaldehyde (1.23 g, 8.2 mmol) in dry THF (20 mL) was added and stirred for 1 hour at −78° C. The mixture was quenched with isopropanol (4.2 mL, 55 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 give benzo[1,3]dioxol-5-yl-(4-methoxy-phenyl)-methanol as an oil (2.54 g, 108% crude yield, HPLC purity 88%): 1H NMR (CDCl3) δ 2.13 (d, J=3 Hz, 1H, OH), 3.79 (s, 3H, —OCH3), 5.72 (d, J=3 Hz, 1H, CH), 5.93 (s, 2H, CH2), 6.74-7.39 (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 1 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

ORD record

ord-49e0e089380c4c54a4f273c36d6b3fd8

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470723B2