Trimethylsilyldiazomethane → 4-Fluoro-3-methoxy-4-methylpent-2-enenitrile

HRID 631438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631438
[F:1][C:2]([CH3:9])([CH3:8])[C:3](=[O:7])[CH2:4][C:5]#[N:6].[CH3:10][Si](C=[N+]=[N-])(C)C>C(OCC)C>[F:1][C:2]([CH3:9])([CH3:8])[C:3]([O:7][CH3:10])=[CH:4][C:5]#[N:6]

Komponenten

4

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 866535074-Fluoro-4-methyl-3-oxopentanenitrile

Produkt 1

HCID 866535164-Fluoro-3-methoxy-4-methylpent-2-enenitrileAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-fluoro-4-methyl-3-oxopentanenitrile (1 g, 7.75 mmol) in dry diethyl ether (150 mL) at 0° C., was added dropwise (trimethylsilyl)diazomethane (4.65 mL of a 2.0 M solution in diethyl ether, 9.30 mmol). After warming to room temperature the reaction mixture was stirred for a further 15 h. The reaction mixture was concentrated under reduced pressure to afford 4-fluoro-3-methoxy-4-methylpent-2-enenitrile as a yellow oil (1 g, 91%) which was taken on to the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 4.89 (s, 1H), 4.23 (s, 3H), 1.47 (d, J=21 Hz, 6H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-40ead9ace1ec48a8880db04f7666eebd
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320739B2

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