3-Chloropropiophenone → 1-Chloro-3-phenylhex-5-en-3-ol

HRID 406609

Reaktionsgleichung

Reaktionsgleichung von HRID 406609
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH2:12]([Mg]Br)[CH:13]=[CH2:14]>C1COCC1>[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([OH:5])[CH2:14][CH:13]=[CH2:12]

Komponenten

4

Edukt 2

HCID 702953-ChloropropiophenoneHCID 178455850HCID 178455850, Verbindung

Produkt 1

HCID 159334751-Chloro-3-phenylhex-5-en-3-olAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 3-chloro-1-phenylpropan-1-one (170 g, 1.01 mol) in anhydrous THF (1200 mL) was added allylmagnesium bromide (1.2 L, 1 mol/L) at −78° C. under nitrogen. The formed mixture was stirred for 30 min at −78° C. The reaction was quenched with aqueous NaHCO3 solution. The organic phase was separated, dried over Na2SO4 and concentrated to give the crude product, which was purified by column chromatography (petroleum ether/EtOAc=100:1) to afford 1-chloro-3-phenylhex-5-en-3-ol (180 g, 86%). 1H NMR (CDCl3): 2.27 (m, 2H), 2.51 (m, 1H), 2.74 (m, 1H), 3.22 (m, 1H), 3.58 (m, 1H), 5.16 (m, 2H), 5.53 (m, 1H), 7.23 (m, 1H), 7.39 (m, 4H).

Aufarbeitung

  1. customThe reaction was quenched with aqueous NaHCO3 solution
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by column chromatography (petroleum ether/EtOAc=100:1)

Quellen und Nachweise

ORD-Eintrag
ord-2654862977964e27b55ce369721df40c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754076B2

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