1-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene → 2-But-1-ynyl-5-fluoro-phenol

HRID 423180

Reaktionsgleichung

Reaktionsgleichung von HRID 423180
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[O:12]COC)#[C:2][CH2:3][CH3:4]>Cl.CC(C)=O.CCOCC>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[OH:12])#[C:2][CH2:3][CH3:4]

Komponenten

5

Edukt 1

HCID 595651761-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene

Produkt 1

HCID 595651802-But-1-ynyl-5-fluoro-phenolAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene (6.1 g, 29 mmol) is dissolved in 250 mL of a 10% solution of concentrated HCl in acetone. The solution is stirred at room temperature for 5 h. The reaction is diluted with ether and washed with saturated aqueous NaHCO3 and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (Biotage® Si65M, 5% AcOEt/hexane) to yield 3.52 g (73%) of the title compound as an orange oil. GCMS m/e 164[M]+.

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic portion is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by flash chromatography (Biotage® Si65M, 5% AcOEt/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9f4eded38863413c8b61709ddb5a6b2b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101761B2

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