Toluene → 1-(2-Methyl-1,3-dioxolan-2-yl)-2-(1-hydroxy-2,3,4,5-tetramethyl-2-cyclopentenyl)benzene

HRID 15694

Reaktionsgleichung

[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2Br)[O:6][CH2:5][CH2:4][O:3]1.C([Li])CCC.[CH3:19][C:20]1[C:21](=[O:28])[CH:22]([CH3:27])[CH:23]([CH3:26])[C:24]=1[CH3:25].C1(C)C=CC=CC=1>O1CCCC1.CCCCCC.O>[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:21]2([OH:28])[CH:22]([CH3:27])[CH:23]([CH3:26])[C:24]([CH3:25])=[C:20]2[CH3:19])[O:6][CH2:5][CH2:4][O:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

Under a nitrogen atmosphere, a solution of 2-(2-methyl-1,3-dioxolan-2-yl)-bromobenzene (1.22 g, 5.0 mmol) in tetrahydrofuran (7.3 g) was cooled to −10° C. and a solution of n-butyllithium in n-hexane (1.56 M, 3.4 mL) was added dropwise thereto. After keeping the temperature for 1 hr, a solution of 2,3,4,5-tetramethylcyclopentenone (0.73 g, 5.3 mmol) in tetrahydrofuran (4.9 g) was added dropwise to the mixture. After raising the temperature to 25° C., the mixture was stirred for 3 hrs. After quenching the reaction by addition of toluene and water, the aqueous layer was removed. The obtained organic layer was washed with saturated brine and then dried over sodium sulfate, and the solvent was removed. After concentration, the residue was washed with cooled hexane to give 1-(2-methyl-1,3-dioxolan-2-yl)-2-(1-hydroxy-2,3,4,5-tetramethyl-2-cyclopentenyl)benzene (0.53 g, yield 35.0%).

Aufarbeitung

customfor 1 hr
customAfter quenching
customthe reaction
customthe aqueous layer was removed
washThe obtained organic layer was washed with saturated brine
dry with materialdried over sodium sulfate
customthe solvent was removed
concentrationAfter concentration
washthe residue was washed with cooled hexane

Quellen und Nachweise

ORD-Eintrag: ord-39da437e9a8f4fa7a9c615c95176064a
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07732643B2

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