Chloride → 4-Azido-7-cyanochroman

HRID 32051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 32051
Cl[CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[N-:14]=[N+:15]=[N-:16].[Na+].C1(C)C=CC=CC=1.[Cl-]>CN(C=O)C>[N:14]([CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1)=[N+:15]=[N-:16]

Komponenten

6

Edukt 4

HCID 312ChlorideHCID 1140TolueneHCID 33557Sodium AzideHCID 18448592HCID 18448592, Verbindung

Produkt 1

HCID 184485894-Azido-7-cyanochroman

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-Chloro-7-cyanochroman (Step C) (8.1 g, 42 mmol) was dissolved in dry DMF (90 mL) and NaN3 (4.0 g, 62 mmol) was added and the reaction was heated to 80° C. under N2. After 5 h TLC (SiO2, toluene) showed that no starting chloride was present. The reaction was cooled and partitioned between EtOAc (200 mL) and H2O (150 mL). The organic phase was washed with H2O (2×100 mL) and brine (100 mL). The solution was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified by column chromatography (SiO2, 15% EtOAc in hexane) to provide the title compound.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. custompartitioned between EtOAc (200 mL) and H2O (150 mL)
  3. washThe organic phase was washed with H2O (2×100 mL) and brine (100 mL)
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a residue which
  8. customwas purified by column chromatography (SiO2, 15% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-98fd8387528a469cbcf5e2db00cdee14
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425631B2

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