N-Hydroxyphthalimide → 8-Methoxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-one

HRID 61903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 61903
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:18][C:17]3[C:16]4[N:15]=[CH:14][CH:13]=[CH:12][C:11]=4[O:10][C:9]=3[C:8]([CH3:20])([CH3:19])[C:7]=2[CH:21]=1.Cl([O-])=[O:23].[Na+].ON1C(=O)C2=CC=CC=C2C1=O>CC#N.O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:23])[C:17]3[C:16]4[N:15]=[CH:14][CH:13]=[CH:12][C:11]=4[O:10][C:9]=3[C:8]([CH3:19])([CH3:20])[C:7]=2[CH:21]=1

Komponenten

7

Edukt 3

HCID 10665N-HydroxyphthalimideHCID 23668197Sodium ChloriteHCID 66835156HCID 66835156, Verbindung

Produkt 1

HCID 668342278-Methoxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-oneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

8-Methoxy-10,10-dimethyl-5,10-dihydro-11-oxa-4-aza-benzo[b]fluorene (Compound GT15-3, 22 mg) was dissolved in MeCN (0.26 ml) and water (0.13 ml), added with sodium chlorite (14 mg) and N-hydroxyphthalimide (2.6 mg), and the mixture was stirred at 40° C. for 1 hr. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (16 mg, 70%).

Aufarbeitung

  1. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b11ea20fef8e4e89b63af107aefac0a8
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440922B2

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