2-(3-Chlorophenyl)-2-methylpropanal → 3-(3-Chlorophenyl)-3-methylbutan-2-ol

HRID 83867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83867
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:13][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[CH:9]([OH:10])[CH3:13])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 820751242-(3-Chlorophenyl)-2-methylpropanalHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 667407143-(3-Chlorophenyl)-3-methylbutan-2-olAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 2-(3-chlorophenyl)-2-methylpropanal (4.6 g, 25.7 mmol) in THF (150 mL) at 0° C. was added MeMgBr (3M in ether, 17.1 mL, 51.3 mmol, 2 eq) dropwise over 2 h. After stirring 1 h at 0° C., the reaction was allowed to warm to room temperature, quenched with 1N HCl and then extracted with EtOAc. The extracts were dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography (silica, Hex/EtOAc=20:1 to 10:1) to give 3-(3-chlorophenyl)-3-methylbutan-2-ol (3.9 g, 78%). 1H NMR (400 MHz, CDCl3) δ 7.36 (s, 1H), 7.28 (m, 2H), 7.18 (m, 1H), 3.85 (q, 1H), 1.32 (d, J=6.4 Hz, 6H), 1.05 (d, J=6.8 Hz, 3H).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customquenched with 1N HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe extracts were dried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography (silica, Hex/EtOAc=20:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-1fac463ae16c490bb91b476bfa4fc554
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846739B2

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