Ethyl Acetate → (4S)-Oct-1-yn-4-ol

HRID 427063

Reaktionsgleichung

Reaktionsgleichung von HRID 427063
C([O:9][C@@H:10]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][C:12]#[CH:13])(=O)C1C=CC=CC=1.[OH-].[K+].OC(CCCC)CC#C.C(OCC)(=O)C>CO.O>[OH:9][C@@H:10]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][C:12]#[CH:13]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 1036561-Octyn-4-olHCID 53798844HCID 53798844, Verbindung

Produkt 1

HCID 12786164(4S)-Oct-1-yn-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

A solution of 1.15 g (5.0 mmoles) of (S)-4-benzoyloxy-1-octyne (Example 141) and 1.40 g (25 mmoles) of potassium hydroxide in 50 ml of 10:1 methanol-water is allowed to stand at room temperature for 24 hours. The bulk of the methanol is evaporated at room temperature, and the mixture is extracted with ether. The extract is washed with brine, dried over magnesium sulfate, and evaporated to give a colorless oil, identical to 4-hydroxy-1-octyne [α]D25 =+17±1.0° (C=0.77, ethyl acetate). This compound has the (S)-configuration.

Aufarbeitung

  1. customThe bulk of the methanol is evaporated at room temperature
  2. extractionthe mixture is extracted with ether
  3. washThe extract is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-a5b941e0bc15442eb856ebe53e969af4
Quelldatensatz
uspto-grants-1979_10
Patentnummer
US04172839

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