Ammonium Chloride → 1-(3-Ethyl-1-benzofuran-2-yl)-3-methylbutan-1-ol

HRID 2091018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091018
[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:12]=[O:13])[CH3:2].O1CCCC1.[CH2:19]([Mg]Br)[CH:20]([CH3:22])[CH3:21].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:12]([OH:13])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:2]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 126115243-Ethyl-1-benzofuran-2-carbaldehydeHCID 178420648HCID 178420648, Verbindung

Produkt 1

HCID 667789351-(3-Ethyl-1-benzofuran-2-yl)-3-methylbutan-1-olAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution (50 mL) of 3-ethyl-1-benzofuran-2-carbaldehyde (2.27 g) synthesized above in tetrahydrofuran was added dropwise 1.0M isobutylmagnesium bromide tetrahydrofuran solution (19.5 mL) at 0° C., and the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio) to give the title object compound (1.55 g, 51%) as a yellow oil.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio)

Quellen und Nachweise

ORD-Eintrag
ord-dad972e7dce74bf7b542bc92372952bf
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436043B2

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