Diethyl Ether → 3-((Benzyloxy)methyl)cyclobutanone

HRID 1641493

Reaktionsgleichung

[CH2:1]([O:8][CH2:9][CH:10]1[CH2:13][C:12](=[O:14])[C:11]1(Cl)Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)C>C(O)(=O)C.[Zn]>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:13][C:12](=[O:14])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Zinc dust (93.5 g, 1.44 mol) was added to a solution of 3-(benzyloxymethyl)-2,2-dichlorocyclobutanone (124 g, 0.48 mol) in glacial acetic acid (800 ml) at room temperature. The reactants were heated at 60° C. for 1 hr, after which time dry diethyl ether was added to the cooled products, which were then filtered. The residue was washed with diethyl ether and the combined filtrate and washings were concentrated under reduced pressure. The residue was dissolved in dichloromethane, which was washed with saturated NaHCO3 twice and water once. The organic phase was dried over MgSO4 and the solvent was evaporated to give an oily product, which was purified by column chromatography (Hexane: EtOAc=6:1).

Aufarbeitung

filtrationwere then filtered
washThe residue was washed with diethyl ether
concentrationthe combined filtrate and washings were concentrated under reduced pressure
dissolutionThe residue was dissolved in dichloromethane
washwhich was washed with saturated NaHCO3 twice
dry with materialThe organic phase was dried over MgSO4
customthe solvent was evaporated
customto give an oily product, which
customwas purified by column chromatography (Hexane: EtOAc=6:1)

Quellen und Nachweise

ORD-Eintrag: ord-5c4b9d4f19c7408b8a692fe16d039bbf
Quelldatensatz: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08114994B2

Verknüpfte Notizen

Wird geladen…