Hydrogen Peroxide → HCID 70859532, Verbindung

Temperatur

0 °C

To a suspension of 4-acetylamino-3-allyl-2-hydroxy-benzoic acid methyl ester (2.49 g, 10 mmol, prepared as described in Takuji Kakigami et. al., Chem. Pharm. Bull, 46 (1), 42-52, (1998)) in THF (10 mL) at 0° C. under Argon was added a 0.5 M solution of 9-BBN in THF (80 mL, 40 mmol). The reaction mixture was stirred at 0° C. for 40 min, then at rt for 2 h. The reaction mixture was then cooled to 0° C., and 1 N aqueous NaOH (25 mL) was added dropwise over 5 min, followed by 30% aqueous H2O2 (20 mL) over 5 min. After addition, the reaction mixture was stirred at rt for 2 h, then extracted with EtOAc (3×60 mL). The combined EtOAc extracts were washed with brine, dried (Na2SO4), and concentrated under reduced pressure to give a crude product, which was chromatographed (silica gel) eluting with 30% to 80% EtOAc/hexane to afford the title compound (1.82 g) as a foam.

1. waitat rt for 2 h
2. temperatureThe reaction mixture was then cooled to 0° C.
3. additionAfter addition
4. stirringthe reaction mixture was stirred at rt for 2 h
5. extractionextracted with EtOAc (3×60 mL)
6. washThe combined EtOAc extracts were washed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure
9. customto give a crude product, which
10. customwas chromatographed (silica gel)
11. washeluting with 30% to 80% EtOAc/hexane

ORD-Eintrag

ord-c74edb8ab2ae433895e7dab8b7cebc9f

Quelldatensatz

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07405234B2