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

HRID 2116818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2116818
[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

8

Edukt 4

HCID 1140TolueneHCID 410922,3,4,5-Tetramethyl-2-cyclopentenoneHCID 6152842-(2-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 178418339Butyllithium

Produkt 1

HCID 230162251-(2-Methyl-1,3-dioxolan-2-yl)-2-(1-hydroxy-2,3,4,5-tetramethyl-2-cyclopentenyl)benzeneAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

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

  1. customfor 1 hr
  2. customAfter quenching
  3. customthe reaction
  4. customthe aqueous layer was removed
  5. washThe obtained organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed
  8. concentrationAfter concentration
  9. washthe residue was washed with cooled hexane

Quellen und Nachweise

ORD-Eintrag
ord-3cfc4a0639df460aa454f22802915d11
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439379B2

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