Hydroxylamine → 2-METHYL-3-PENTYL ACETATE

HRID 279417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279417
NO.[CH:3](=[O:7])[CH:4]([CH3:6])[CH3:5].C([Zn][CH2:11][CH3:12])C.[C:13](OC(=O)C)(=[O:15])[CH3:14]>CCCCCC.C1(C)C=CC=CC=1.ClC1C=CC=CC=1>[C:13]([O:7][CH:3]([CH2:11][CH3:12])[CH:4]([CH3:6])[CH3:5])(=[O:15])[CH3:14]

Komponenten

8

Edukt 4

HCID 787HydroxylamineHCID 6561IsobutyraldehydeHCID 7918Acetic AnhydrideHCID 178418750HCID 178418750, Verbindung

Produkt 1

HCID 5387502-METHYL-3-PENTYL ACETATEAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 7964ChlorobenzeneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A vial was charged with aminoalcohol A (0.0057 g, 0.024 mmol). To the vial was added 1.52 mL of a stock solution containing freshly distilled isobutyraldehyde (0.22 g), chlorobenzene internal standard (0.22 g), 1 M diethylzinc in hexane (6.0 mL), and toluene (3.0 mL). After 48 h acetic anhydride (0.200 mL) was added. After an additional 72 h a sample of the solution was analyzed by gas chromatography at 70° C. on a Cyclodex B stationary phase. The product 3-acetoxy-2-methylpentane was formed in 92% yield and 98% enantiomeric excess. The identity and yield of the product was established by comparison with an authentic sample prepared by treatment of racemic 2-methyl-3-pentanol with acetic anhydride.

Quellen und Nachweise

ORD-Eintrag
ord-43a83852a67a45ada3f287b17d369a56
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362344B1

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