Ethyl Acetate → cis 3a,4,5,7a-tetrahydro-2(3H)-benzofuranone

HRID 846530

Reaktionsgleichung

CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[C:14]([CH2:19][CH:20]1[C:25](=[O:26])[CH:24]=[CH:23][CH2:22][CH2:21]1)([O:16]CC)=O.C(C(C(C([O-])=O)O)O)(O)=O.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1>[O:26]1[C@H:25]2[CH:24]=[CH:23][CH2:22][CH2:21][C@H:20]2[CH2:19][C:14]1=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a solution of 13.5 g (66.0 mmoles) of aluminum isopropoxide in 100 ml of toluene was added 2.0 g (11.0 mmoles) of 6-(carbethoxymethyl)-2-cyclohexen-1-one at room temperature, and the solution was heated to 90° C. for 18 hours. The solution was cooled to room temperature, and aqueous saturated sodium hydrogen tartrate and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate, and the combined ethyl acetate extracts were dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The crude material was purified by Kugelrohr distillation (bp 40°-80° C./0.01 mm Hg) to yield 1.3 g (86%) of cis 3a,4,5,7a-tetrahydro-2(3H)-benzofuranone, as confirmed by NMR and IR data.

Aufarbeitung

temperatureThe solution was cooled to room temperature
extractionThe aqueous layer was extracted with ethyl acetate
dry with materialthe combined ethyl acetate extracts were dried over anhydrous magnesium sulfate
customevaporated under reduced pressure
distillationThe crude material was purified by Kugelrohr distillation (bp 40°-80° C./0.01 mm Hg)

Quellen und Nachweise

ORD-Eintrag: ord-b2d6c0049ace41d3a351d491dc0f1323
Quelldatensatz: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05137035

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