1-Penten-3-one → 2-(2-Hydroxyethyl)-5-methoxy-2-(3-oxopentyl)-1-indanone

HRID 7901

Reaktionsgleichung

Reaktionsgleichung von HRID 7901
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:15].[CH:16]([C:18]([CH2:20][CH3:21])=[O:19])=[CH2:17].C[O-].[Na+]>CO.CCOC(C)=O>[OH:1][CH2:2][CH2:3][C:4]1([CH2:17][CH2:16][C:18](=[O:19])[CH2:20][CH3:21])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:15]

Komponenten

6

Edukt 3

HCID 153941-Penten-3-oneHCID 10942334Sodium MethoxideHCID 219908562-(2-Hydroxyethyl)-5-methoxy-1-indanone

Produkt 1

HCID 219909372-(2-Hydroxyethyl)-5-methoxy-2-(3-oxopentyl)-1-indanoneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 2-(2-hydroxyethyl)-5-methoxy-1-indanone (105 mg, 0.51 mmol) in methanol (2.0 mL) at room temperature was treated with ethyl vinyl ketone (EVK, 0.102 mL) and 0.5M sodium methoxide in methanol (0.204 mL, 0.1 mmol). The mixture was stirred in a capped flask and heated in an oil bath at 60° C. for 8 hours. After cooling, the reaction mixture was diluted with EtOAc (25 mL), washed with 0.2N HCl (15 mL), water (15 mL), and brine (15 mL), dried over MgSO4, filtered, and evaporated under vacuum to afford 2-(2-hydroxyethyl)-5-methoxy-2-(3-oxopentyl)-1-indanone (138 mg, 93% yield) as an oil.

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with 0.2N HCl (15 mL), water (15 mL), and brine (15 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-787cbd4a712c4b168df30fdb5fe09b66
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087599B2

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