Water → (R)-4-phenylbutane-1,2-diol

HRID 278473

Reaktionsgleichung

Reaktionsgleichung von HRID 278473
[BH4-].[Na+].[OH:3][C@H:4]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5](OCC)=[O:6].O>CO>[C:12]1([CH2:11][CH2:10][C@@H:4]([OH:3])[CH2:5][OH:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 2733848Ethyl (R)-2-hydroxy-4-phenylbutyrateHCID 4311764Sodium borohydride

Produkt 1

HCID 10975846(R)-4-phenylbutane-1,2-diolAusbeute 102,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

NaBH4 (1.82 g) was added portionwise to an ice cooled solution of ethyl (R)-2-hydroxy-4-phenylbutyrate (2.0 g) in methanol (40 ml). After the addition was completed, the reaction mixture was stirred at room temperature for 45 minutes. Water (20 ml) was added, and the resulting mixture was stirred for several minutes and then evaporated under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave (R)-4-phenylbutane-1,2-diol (1.63 g) as a colorless oil. This material was used for the next reaction without further purification.

Aufarbeitung

  1. additionAfter the addition
  2. stirringthe resulting mixture was stirred for several minutes
  3. customevaporated under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-433ad11be354462c875b62f1d76f4144
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359145B1

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