Hydride → 3,5-Dichloro-4-(4-methoxyphenoxy)benzyl Alcohol

Temperatur

0 °C

To a solution of 3,5-dichloro-4-(4-methoxy-phenoxy)-benzoic acid ethyl ester (1.36 g, 4.01 mmol) in dichloromethane (35 ml) at 0° C. was added diisobutylaluminun hydride (1M in toluene, 12 ml, 12 mmol) and the mixture was stirred for 2.5 hours at 0° C. The reaction mixture was quenched with potassium sodium tartrate tetrahydrate (0.5 M aqueous solution, 50 ml), stirred for 20 minutes at room temperature and then was filtered through diatomaceous earth. The filtrate was concentrated and then taken up in water (60 ml). The aqueous solution was extracted with ethyl acetate (4×60 ml). The combined extracts were dried, filtered, and concentrated. The residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane) to afford the title compound (871 mg). NMR (400 MHz, CDCl3) δ7.39 (s, 2H), 6.74-6.82 (m, 4H), 4.69 (d, 2H), 3.76 (s, 3H), 1.83 (t, 1 H).

1. customThe reaction mixture was quenched with potassium sodium tartrate tetrahydrate (0.5 M aqueous solution, 50 ml)
2. stirringstirred for 20 minutes at room temperature
3. filtrationwas filtered through diatomaceous earth
4. concentrationThe filtrate was concentrated
5. extractionThe aqueous solution was extracted with ethyl acetate (4×60 ml)
6. customThe combined extracts were dried
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane)

ORD-Eintrag

ord-0133d51d904c4f07ad48b04650104254

Quelldatensatz

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06620830B2