(E)-5-Dimethylamino-1-phenyl-pent-1-en-3-one; hydrochloride → 5-(Dimethylamino)-3-hydroxy-1-phenyl-1-pentene

HRID 46492

Reaktionsgleichung

Reaktionsgleichung von HRID 46492
Cl.[CH3:2][N:3]([CH3:16])[CH2:4][CH2:5][C:6](=[O:15])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>CO.O.O>[CH3:16][N:3]([CH3:2])[CH2:4][CH2:5][CH:6]([OH:15])[CH:7]=[CH:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 3

HCID 145789(E)-5-Dimethylamino-1-phenyl-pent-1-en-3-one; hydrochlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Produkt 1

HCID 545141025-(Dimethylamino)-3-hydroxy-1-phenyl-1-penteneAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

5-(Dimethylamino)-1-phenyl-1-penten-3-one, hydrochloride (1:1) (18.6 g, 0.078 mole) is dissolved in 200 ml 1:1 methanol-water. Sodium bicarbonate (2.0 g) is added, followed by the portionwise addition of NaBH4 (3.0 g) at 35° C. After addition, the reaction mixture is stirred for 2 hours at room temperature. This solution is diluted with 200 ml of water and organics are extracted with ether. The ether is dried with MgSO4, filtered and concentrated in vacuo to yield 14.3 g of product. IR consistent.

Aufarbeitung

  1. additionAfter addition
  2. extractionorganics are extracted with ether
  3. dry with materialThe ether is dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e03dceb46aca4a64826561499e8e0c0e
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04173649

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