Ammonium Chloride → (3R,3aR,6R,6aS)-3-(5-fluoro-2-nitro-phenoxy)-6-methyl-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-6-ol

HRID 1396642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396642
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[O:7][C@@H:8]1[CH2:12][O:11][C@@H:10]2[C:13](=[O:16])[CH2:14][O:15][C@H:9]12.[CH3:21][Li].[NH4+].[Cl-]>C1COCC1.C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[O:7][C@@H:8]1[CH2:12][O:11][C@@H:10]2[C@:13]([CH3:21])([OH:16])[CH2:14][O:15][C@H:9]12

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 86718460(3R,3aR,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-oneHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 86718462(3R,3aR,6R,6aS)-3-(5-fluoro-2-nitro-phenoxy)-6-methyl-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-6-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.6 g (5.7 mmol) (3R,3aR,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-one (III.7) in THF are cooled to −70° C. 3.5 ml (5.7 mmol) 1.6 mol/l methyl lithium in diethyl ether are added dropwise and the reaction mixture is allowed to reach RT and stirred for 2.5 h. Aqueous NH4Cl solution and diethyl ether are added and the organic layer is separated, dried and evaporated. The residue is purified by FC (Al2O3).

Aufarbeitung

  1. customto reach RT
  2. customthe organic layer is separated
  3. customdried
  4. customevaporated
  5. customThe residue is purified by FC (Al2O3)

Quellen und Nachweise

ORD-Eintrag
ord-2c027ff4423e42bfa9b70c25e5197919
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901138B2

Notizen zur Reaktion

Wird geladen…