Acetic Acid → HCID 12025898, Verbindung

HRID 2298626

Reaktionsgleichung

Reaktionsgleichung von HRID 2298626
[C:1]([C:5]1[O:9][C:8]([CH3:10])=[C:7](C(Cl)=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si](C=[N+]=[N-])(C)C.[BrH:21].[C:22]([OH:25])(=O)[CH3:23]>C(#N)C>[C:1]([C:5]1[O:9][C:8]([CH3:10])=[C:7]([C:22](=[O:25])[CH2:23][Br:21])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 167693TrimethylsilyldiazomethaneHCID 27984945-(Tert-Butyl)-2-Methylfuran-3-Carbonyl Chloride

Produkt 1

HCID 12025898HCID 12025898, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 1 g (5 mmol) of 5-(tert-butyl)-2-methylfuran-3-carbonyl chloride (Maybridge, Cornwall, UK) dissolved in dry acetonitrile (4 mL) and 6.25 mL (12.5 mmol) of 2 M trimethylsilyldiazomethane in hexanes (Aldrich, Milwaukee, Wis.) was stirred 1.75 h at room temperature and the mixture was cooled on an ice bath for 5 min. To this, 30% hydrogen bromide in acetic acid (2 mL, 10 mmol) was added dropwise over 10 min. This was stirred an additional 20 minutes on an ice bath. Evaporation of the solvents gave 1-[5-(tert-butyl)-2-methyl(3-furyl)]-2-bromoethan-1-one (1 g, 77%) as a brown oil. 1H-NMR (DMSO-d6; 300 MHz) δ6.50 (s, 1H), 4.57(s, 2H), 2.52 (s, 1H), 1.24 (s, 9H). Mass spectrum (LCA, m/z): Calcd. for C11H15O2Br, 259.1 and 261.1 (M+H), found 259.1 and 261.1.

Aufarbeitung

  1. temperaturethe mixture was cooled on an ice bath for 5 min
  2. customEvaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-175a621a15c04ba6b0cead3d192e5b80
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06492403B1

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