Isoamyl Nitrite → (6E)-2-bromo-6-hydroxyimino-8,9-dihydro-7H-benzo[7]annulen-5-one

HRID 2407584

Reaktionsgleichung

Reaktionsgleichung von HRID 2407584
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1.[N:14](OCCC(C)C)=[O:15]>CCOCC.O1CCCC1.Cl.CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])/[C:10](=[N:14]/[OH:15])/[CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1

Komponenten

6

Edukt 2

HCID 8053Isoamyl NitriteHCID 102433122-bromo-6,7,8,9-tetrahydro-5H-benzo(7)annulen-5-one

Produkt 1

HCID 57816546(6E)-2-bromo-6-hydroxyimino-8,9-dihydro-7H-benzo[7]annulen-5-oneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 21868444Ether tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
24 °C

Versuchsvorschrift

J.3, 2-Bromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (1.5 g, 5.9 mmol) was dissolved in 2:1 ether/tetrahydrofuran (120 mL) and 1N HCl in ether (9 mL) was added. The solution was cooled to 0° C. before addition of isoamyl nitrite (1.2 mL, 9 mmol) and the reaction was stirred 18 h at 24° C., concentrated, and applied to 25 (M) Biotage silica gel column. Gradient elution from 15-100% B (A=Hexanes; B=ethyl acetate) over 1 L and gave J.3a (E)-2-bromo-6-(hydroxyimino)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one 1 g (64%). LC (Cond.-J1); RT=1.9 min; LC/MS: Anal. Calcd. for [M+H]+ C11H10NBrO2: 268; found: 268.

Aufarbeitung

  1. additionwas added
  2. concentrationconcentrated
  3. washGradient elution from 15-100% B (A=Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a56b48fc623d4cb699e573009d3db8fb
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809548B2

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