1-Butanaminium, N,N,N-tributyl-, azide → (S)-3-Azido-4,4-dimethyldihydrofuran-2(3H)-one

HRID 520351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520351
FC(F)(F)S(O[C@@H:7]1[C:11]([CH3:13])([CH3:12])[CH2:10][O:9][C:8]1=[O:14])(=O)=O.[N-:17]=[N+:18]=[N-:19].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.CCOC(C)=O>[N:17]([C@H:7]1[C:11]([CH3:13])([CH3:12])[CH2:10][O:9][C:8]1=[O:14])=[N+:18]=[N-:19]

Komponenten

5

Edukt 2

HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 10106752(R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl trifluoromethanesulfonate

Produkt 1

HCID 10057735(S)-3-Azido-4,4-dimethyldihydrofuran-2(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl trifluoromethanesulfonate (10 g) in DCM (10 mL) was added tetra-n-butylammonium azide (11.1 g). The reaction mixture was stirred at rt for 16 hr. The reaction was diluted with EtOAc, washed with water, sat. NaHCO3, citric acid, water, and sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated to yield an oil. The crude product was purified by silica gel chromatography (0-100% EtOAc in hexane) to yield (S)-3-azido-4,4-dimethyldihydrofuran-2(3H)-one as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 3.87-4.02 (3H, m), 1.17 (3H, s), 1.02 (3H, s).

Aufarbeitung

  1. washwashed with water, sat. NaHCO3, citric acid, water, and sat. NaCl
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield an oil
  6. customThe crude product was purified by silica gel chromatography (0-100% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c51c2f503c1544b8b3d69fba829277c1
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326973B2

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