Water → (RS)-2-(2-buten-1-yl)-6-methoxy-1-indanone

HRID 264369

Reaktionsgleichung

Reaktionsgleichung von HRID 264369
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[CH3:13][CH:14](O)[CH:15]=[CH2:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:13]([CH:8]1[CH2:7][C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]1=[O:12])[CH:14]=[CH:15][CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 3340366-Methoxy-1-Indanone

Produkt 1

HCID 54031441(RS)-2-(2-buten-1-yl)-6-methoxy-1-indanoneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 64952,2-DimethoxypropaneLösungsmittel

Versuchsvorschrift

A solution of 9.3 g of 6-methoxy-1-indanone, 11.8 ml of 3-buten-2-ol and 100 mg of p-toluenesulfonic acid in 100 ml of 2,2-dimethoxypropane was boiled under reflux for 64 hours on a water separator filled with molecular sieve (0.4 nm, 2 mm pearl shaped). The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 4:1). 9.2 g (74%) of (RS)-2-(2-buten-1-yl)-6-methoxy-1-indanone were obtained as a yellow oil.

Aufarbeitung

  1. additionseparator filled with molecular sieve (0.4 nm, 2 mm pearl shaped)
  2. concentrationThe reaction mixture was subsequently concentrated in a vacuum
  3. custompurified by column chromatography on silica gel (hexane/diethyl ether 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-f8c16da946564058816e57fa74d5bb5d
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646173

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