Aluminium lithium hydride → (3-Butyl-5-methyl-isoxazol-4-yl)-methanol

HRID 1942278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942278
C([O:3][C:4]([C:6]1[C:7]([CH2:12][CH2:13][CH2:14][CH3:15])=[N:8][O:9][C:10]=1[CH3:11])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:12]([C:7]1[C:6]([CH2:4][OH:3])=[C:10]([CH3:11])[O:9][N:8]=1)[CH2:13][CH2:14][CH3:15]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 665992233-Butyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 66599297(3-Butyl-5-methyl-isoxazol-4-yl)-methanolAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-butyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester (9.8 g, 46.3 mmol) in THF (100 mL) under argon and at 0° C. was added lithium aluminium hydride (2.03 g, 53.4 mmol) in five portions. After 1 h the reaction mixture was quenched dropwise with Seignette salt solution. The reaction mixture was filtered and the filtrate extracted with ethyl acetate. The combined organic extracts were washed with Seignette salt solution then dried, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 4:6) afforded the title compound (7.5 g, 95%) as a yellow liquid. MS: m/e=170.3 [M+H]+.

Aufarbeitung

  1. customAfter 1 h the reaction mixture was quenched dropwise with Seignette salt solution
  2. filtrationThe reaction mixture was filtered
  3. extractionthe filtrate extracted with ethyl acetate
  4. washThe combined organic extracts were washed with Seignette salt solution
  5. customthen dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica, heptane:ethyl acetate=100:0 to 4:6)

Quellen und Nachweise

ORD-Eintrag
ord-fe88e2268466450c8a7773ad943b22c4
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389550B2

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