Quinone → Spiro[2.4]hept-5-ene-4,7diol Diacetate

HRID 1392932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392932
[OH2:1].O.[C:3]([O-:6])(=[O:5])[CH3:4].[Li+].[Cl-].[Li+].[C:10]1(=[O:17])[CH:15]=CC(=O)C=C1.[CH2:18]1[C:20]2([CH:24]=[CH:23][CH:22]=[CH:21]2)[CH2:19]1>C(O)(=O)C.O.CCCCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[O-2].[Mn+4].[O-2]>[C:3]([O:6][CH:21]1[CH:22]=[CH:23][CH:24]([O:1][C:10](=[O:17])[CH3:15])[C:20]21[CH2:19][CH2:18]2)(=[O:5])[CH3:4]

Komponenten

10

Edukt 4

HCID 4650QuinoneHCID 136590Spiro(2,4)hepta-4,6-dieneHCID 433294Lithium ChlorideHCID 23666338Lithium acetate dihydrate

Produkt 1

HCID 131726807Spiro[2.4]hept-5-ene-4,7diol DiacetateAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 167845palladium(II) acetateKatalysatorHCID 178418406HCID 178418406, VerbindungKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8003PentaneLösungsmittel

Versuchsvorschrift

To a two phase mixture of palladium acetate (1.7 g), lithium acetate dihydrate (123.6 g), lithium chloride (30.0 g), manganese (IV) oxide (15.3 g) and p-benzoquinone (1.4 g) in acetic acid (250 ml), water (420 ml) and pentane (3.7 l) was added spiro[2.4]hepta-4,6-diene (7.7 g) and the resulting mixture was stirred at ambient temperature for 24 hours. The reaction mixture was filtered through a celite plug washing with pentane (1 l). The organic phase was collected, washed successively with saturated sodium bicarbonate solution (500 ml), water (500 ml) and brine (100 ml) then concentrated to dryness under reduced pressure. The residue was absorbed onto silica and purified by chromatography (SiO2; 9:1 isohexane:ethyl acetate) to afford the subtitle compound (2.1 g).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a celite plug
  2. washwashing with pentane (1 l)
  3. customThe organic phase was collected
  4. washwashed successively with saturated sodium bicarbonate solution (500 ml), water (500 ml) and brine (100 ml)
  5. concentrationthen concentrated to dryness under reduced pressure
  6. customThe residue was absorbed onto silica
  7. custompurified by chromatography (SiO2; 9:1 isohexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0a22a7c1c0104482926a5b32dbb902d2
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345047B2

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