Diisobutylaluminum hydride → HCID 66727644, Verbindung

HRID 1698219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698219
[Br:1][C:2]1[CH:6]=[C:5](/[CH:7]=[N:8]/[S:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[O:4][N:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[CH:6]=[C:5]([CH2:7][NH:8][S:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[O:4][N:3]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 87126736HCID 87126736, Verbindung

Produkt 1

HCID 66727644HCID 66727644, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a chilled (−78° C.) yellow solution of 2-methyl-propane-2-sulfinic acid 1-(3-bromo-isoxazol-5-yl)-meth-(E)-ylideneamide (129 mg, 0.462 mmol) in THF (7 mL) was added a 1 M solution of DIBAH (1.2 mL, 1.2 mmol) in hexanes dropwise. After 1.5 hours, the reaction was quenched with MeOH (4 mL) and the cold bath was removed. The mixture was concentrated in vacuo and the residue was treated with 1 N aqueous NaOH (10 mL) and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 2-methyl-propane-2-sulfinic acid (3-bromo-isoxazol-5-ylmethyl)-amide which was used without further purification. MS m/z 281.35 (M), 283.32 (M+2).

Aufarbeitung

  1. customthe reaction was quenched with MeOH (4 mL)
  2. customthe cold bath was removed
  3. concentrationThe mixture was concentrated in vacuo
  4. additionthe residue was treated with 1 N aqueous NaOH (10 mL)
  5. extractionextracted with EtOAc (3×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fefc8c92c1b84a62b4557d011f722a6b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163918B2

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