Sodium Azide → 2-azido-4-fluoro-2,3-dihydro-1H-inden-1-one

HRID 646718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646718
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[N-:12]=[N+:13]=[N-:14].[Na+]>CC#N>[N:12]([CH:5]1[CH2:4][C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])[C:6]1=[O:11])=[N+:13]=[N-:14]

Komponenten

4

Edukt 2

HCID 33557Sodium Azide2×HCID 121749864-Fluoro-1-indanone

Produkt 1

HCID 866078392-azido-4-fluoro-2,3-dihydro-1H-inden-1-oneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 4-fluoro-2,3-dihydro-1H-inden-1-one (1.29 g, 9.34 mmol) and HNIB (5.02 g, 12.1 mmol) in CH3CN (190.0 mL) was refluxed for 1.5 h, until the solution was clear yellow. Upon cooling to r.t., NaN3 (1.21 g, 18.7 mmol) was added and the solution was stirred at r.t. for 12 h. Additional NaN3 (0.50 g, 7.7 mmol) was added and the solution stirred further at r.t. for 4 h. The reaction mixture was concentrated in vacuo, and the residue was taken up in CH2Cl2 (100 mL). This solution was washed with H2O (75 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified via column chromatography (SiO2, 5:1 hexanes/EtOAc) to give 1.61 g (96% yield) of 2-azido-4-fluoro-2,3-dihydro-1H-inden-1-one: 1H NMR (400 MHz, CDCl3): 7.59 (d, 1H), 7.41 (m, 1H), 7.32 (t, 1H), 4.15 (dd, 1H), 3.55 (dd, 1H), 2.89 (dd, 1H).

Aufarbeitung

  1. stirringthe solution stirred further at r.t. for 4 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washThis solution was washed with H2O (75 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via column chromatography (SiO2, 5:1 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6a63e3e72a3e44ae9245d8ed18aa04b4
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704995B2

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