3-Hydroxy-2,2-diphenylpropanenitrile → HCID 18626554, Verbindung

HRID 1685307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685307
[OH:1][CH2:2][C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]#[N:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[NH2:5][CH2:4][C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][OH:1]

Komponenten

4

Edukt 2

HCID 202707253-Hydroxy-2,2-diphenylpropanenitrileHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 18626554HCID 18626554, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 3-hydroxy-2,2-diphenylpropanenitrile in tetrahydrofuran (50 mL) was slowly added dropwise to a suspension of LAH in tetrahydrofuran (20 mL) at 23° C. The reaction was stirred overnight, then quenched with sodium sulfate decahydrate. The resulting solid was removed by filtration and the filtrate was concentrated to dryness to give the title material (0.45 g, 88%) as an oil which was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 2.49 (2H, s), 3.77 (1H, ddd, J=6.63, 4.23 and 2.53 Hz), 3.82 (2H, s), 4.30 (2H, s), 7.25-7.36 (10H, m). LC/MS (M+H)+: 228. HPLC ret. time (Condition A): 1.228 min.

Aufarbeitung

  1. customquenched with sodium sulfate decahydrate
  2. customThe resulting solid was removed by filtration
  3. concentrationthe filtrate was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9caa8114c2f0461f936be1f2ba086ac4
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148400B2

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