2,2-Dimethyl-1,3-dioxane-4,6-dione → Ethyl 6-(benzyloxy)-3-oxohexanoate

HRID 733181

Reaktionsgleichung

[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1(C)[O:23]C(=O)[CH2:20][C:18](=O)[O:17]1.CN(C1C=CC=CN=1)C.ClC(OC(C)=C)=O.S([O-])(O)(=O)=O.[K+]>C(Cl)Cl>[CH2:18]([O:17][C:16](=[O:23])[CH2:15][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

4-Benzyloxybutyric acid (6.38 mL), Meldrum's acid (5.76 g) and dimethylaminopyridine (9.77 g) were dissolved in DCM (200 mL) and cooled to 0° C. A solution of isopropenyl chloroformate in dichloromethane (100 mL) was added dropwise and stirring at 0° C. continued for a further 2 h. Potassium hydrogen sulphate (200 mL of a 10% aqueous solution) was then added, the organic phase separated, dried over sodium sulphate, and evaporated under reduced pressure. The residue was dissolved in ethanol (200 mL) and heated at reflux overnight. Following cooling, the solvent was evaporated under reduced pressure and the resultant oil was purified by flash silica column chromatography. 6-Benzyloxy-3-oxo-hexanoic acid ethyl ester was isolated as an orange oil (8.53 g).

Aufarbeitung

customthe organic phase separated
dry with materialdried over sodium sulphate
customevaporated under reduced pressure
dissolutionThe residue was dissolved in ethanol (200 mL)
temperatureheated
temperatureat reflux overnight
temperatureFollowing cooling
customthe solvent was evaporated under reduced pressure
customthe resultant oil was purified by flash silica column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-89951e2fd3ce4e01a09824d7d1d6ead2
Quelldatensatz: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07589095B2

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