3-Methyl-2-cyclohexen-1-one → (2R,3R)-7-methyl-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-6-ene

HRID 715488

Reaktionsgleichung

[C:1]1([C@@H:7]([OH:16])[C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][C:18]1[CH2:23][CH2:22][CH2:21][C:20](=O)[CH:19]=1>C1C=CC=CC=1.CCOCC.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>[CH3:17][C:18]1[CH2:23][CH2:22][CH2:21][C:20]2([O:9][C@H:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:16]2)[CH:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 115 °C

Versuchsvorschrift

(1R,2R)-1,2-diphenyl-1,2-ethanediol (150 g, 699 mmol) and 3-methyl-2-cyclohexen-1-one (77 g, 699 mmol) were suspended in benzene (1398 mL) and treated with PPTS (4.39 g, 17.48 mmol). The flask was fitted with a Dean-Stark trap filled with benzene and a condenser. The reaction was heated to 115° C. for 3 days, and then the reaction was cooled to ambient temperature and diluted with ether. The mixture was washed with saturated aq NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated to give a red/orange liquid (214 g, 100% yield). The liquid was used without further purification.

Aufarbeitung

customThe flask was fitted with a Dean-Stark trap
temperaturethe reaction was cooled to ambient temperature
washThe mixture was washed with saturated aq NaHCO3
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-e2fd549a67fb4e3d9ed1a4dad0240270
Quelldatensatz: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09187464B2

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