Aluminium lithium hydride → 2-(4-Aminomethyl-3-fluoro-phenyl)-propan-2-ol

HRID 984801

Reaktionsgleichung

Reaktionsgleichung von HRID 984801
[F:1][C:2]1[CH:9]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([C:10]([OH:13])([CH3:11])[CH3:12])=[CH:9][C:2]=1[F:1]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 224816262-Fluoro-4-(2-hydroxypropan-2-yl)benzonitrile

Produkt 1

HCID 224816482-(4-Aminomethyl-3-fluoro-phenyl)-propan-2-olAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 1.95 g (0.011 mol) 2-fluoro-4-(1-hydroxy-1-methyl-ethyl)-benzonitrile in 30 mL anhydrous THF at 0° C. was added dropwise 34 mL (0.034 mol) 1.0M LiAlH4. The mixture was warmed to room temperature then heated to reflux for 30 minutes. The mixture was then cooled to 0° C. and quenched with 20 mL MeOH added dropwise. Next, it was diluted with 700 mL CHCl3 and washed with 100 mL water. The resulting suspension was filtered through Celite and the organic layer dried over MgSO4 and concentrated to give 1.6 g of an amber oil.

Aufarbeitung

  1. temperaturethen heated
  2. temperatureto reflux for 30 minutes
  3. temperatureThe mixture was then cooled to 0° C.
  4. customquenched with 20 mL MeOH
  5. additionadded dropwise
  6. additionNext, it was diluted with 700 mL CHCl3
  7. washwashed with 100 mL water
  8. filtrationThe resulting suspension was filtered through Celite
  9. dry with materialthe organic layer dried over MgSO4
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f14f133364ed4de89062df99598d69be
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06869945B2

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