Aluminium lithium hydride → 5-(Hydroxymethyl)-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzonitrile

HRID 920284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920284
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=2)=[C:6]([C:21]#[N:22])[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][N:12]=2)=[C:6]([CH:5]=1)[C:21]#[N:22]

Komponenten

5

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 668253413-Cyano-4-(5-trifluoromethyl-pyridin-2-yloxy)-benzoic acid methyl ester

Produkt 1

HCID 668256575-(Hydroxymethyl)-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzonitrileAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-55 °C

Versuchsvorschrift

To a solution of 3-cyano-4-(5-trifluoromethyl-pyridin-2-yloxy)-benzoic acid methyl ester (23 g, 0.070 mol) in anhydrous THF (200 mL), was added LiAlH4 (4.07 g, 0.11 mmol) portionwise at −78° C. The reaction mixture was warmed to −55° C. slowly and stirred for 20 mins, diluted with water (3 mL 0.16 mmol, slow addition), filtered and concentrated. Purification via FC (PE/EtOAc=10/1 to 5/1) afforded the title product as a colorless oil (12.5 g).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customPurification via FC (PE/EtOAc=10/1 to 5/1)

Quellen und Nachweise

ORD-Eintrag
ord-fde3559987d24f0fb0278193cb60faaf
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273054B2

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