Sucrose → HCID 57026341, Verbindung

HRID 1586303

Reaktionsgleichung

Reaktionsgleichung von HRID 1586303
C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.[OH:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[C:30](=[O:34])[CH:29]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:28]2.COC1C=CC(C=O)=CC=1>C(O)C>[OH:34][C@@H:30]1[C:31]2[C:27](=[CH:26][C:25]([OH:24])=[CH:33][CH:32]=2)[CH2:28][C@H:29]1[C:35]([O:37][CH2:38][CH3:39])=[O:36]

Komponenten

5

Edukt 3

HCID 5988SucroseHCID 312444-MethoxybenzaldehydeHCID 212182395-Hydroxy-2-carboethoxy-1-indanone

Produkt 1

HCID 57026341HCID 57026341, VerbindungAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Twenty grams of bakers' yeast (Sigma Chemical Company, type II) are suspended in an aqueous solution containing 30 grams of sucrose in a conical flask, and the mixture is placed on an orbital shaker (220 rpm) at 30° C. for 30 minutes to initiate fermentation. Two grams of 5-hydroxy-2-carboethoxy-1-indanone is dissolved in 2 ml of 95% ethanol, the resulting solution is added to the fermenting yeast, and shaking is resumed. The reaction is followed by TLC (staining with anisaldehyde) to monitor the consumption of starting material and the production of product alcohol. After approximately 48 hours the reaction is judged complete, and the reaction is terminated by removing from the shaker and adding 20-30 grams of Celite. The resulting suspension is suction filtered through a pad of Celite and the clear yellow filtrate is extracted with ethyl acetate (4×200 ml). The extracts are combined, dried over MgSO4, filtered, and rotary evaporated to leave 1.5 grams of (1S,2R)-1-hydroxy-2-carboethoxy-5-hydroxyindane as a yellowish oil (>95% enantiomeric excess as judged by chiral chromatography).

Aufarbeitung

  1. additionthe resulting solution is added to the fermenting yeast
  2. customthe consumption of starting material
  3. waitAfter approximately 48 hours the reaction is judged complete
  4. customthe reaction is terminated
  5. customby removing from the shaker
  6. additionadding 20-30 grams of Celite
  7. filtrationfiltered through a pad of Celite
  8. extractionthe clear yellow filtrate is extracted with ethyl acetate (4×200 ml)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customrotary evaporated

Quellen und Nachweise

ORD-Eintrag
ord-8c6135d33e614798aac8e1e79d2a7f8b
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05942644

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