Isopropanol → HCID 61087120, compound

Temperature

-78 °C

A stirred mixture of 6-bromo-2,3-dihydro-benzo[1,4]dioxine (1.59 g, 7.4 mmol) and dry TRF (10 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 3-methoxy-benzaldehyde (0.92 g, 6.7 mmol) in dry THF (10 mL) was added and stirred for 1 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 (3×30 mL). The combined organic phases were washed with water (2×30 mL), dried over MgSO4 and concentrated to give (2,3-dihydro-benzo[1,4]dioxin-6-yl)-(3-methoxy-phenyl)-methanol as an oil (2.09 g, 114% crude yield). The product was used in the next step without further purification.

1. customdry TRF (10 mL)
2. customevacuated
3. additionrefilled with nitrogen for 10 cycles
4. additionwas added
5. stirringstirred for 1 hour at −78° C
6. extractionThe mixture was extracted with EtOAc (3×30 mL)
7. washThe combined organic phases were washed with water (2×30 mL)
8. dry with materialdried over MgSO4
9. concentrationconcentrated

ORD record

ord-ea9185e6715e476381ec4aeb10e3dff1

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470723B2