Hydrogen Peroxide → cis-7-Methyl-1,4-dioxa-spiro[4.5]decan-8-ol

HRID 1028203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028203
[CH3:1][CH:2]1[C:11](=[O:12])[CH2:10][CH2:9][C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3]1.CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[OH-].[Na+].OO>O1CCCC1>[CH3:1][C@H:2]1[C@@H:11]([OH:12])[CH2:10][CH2:9][C:4]2([O:5][CH2:6][CH2:7][O:8]2)[CH2:3]1

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2706287-Methyl-1,4-dioxaspiro[4.5]decan-8-oneHCID 4304157Potassium;tri(butan-2-yl)boranuide

Produkt 1

HCID 13378641cis-7-Methyl-1,4-dioxa-spiro[4.5]decan-8-olAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a tetrahydrofuran (100 mL) solution of 7-methyl-1,4-dioxa-spiro[4.5]-decan-8-one (Tetrahedron Asymmetry 2001, 12, 1683) (9.50 g), K-Selectride (1.0 mol/L tetrahydrofuran solution, 65 mL) was gradually added at −78° C. After 1 hour, the reaction mixture was warmed to 0° C., and a 1 N aqueous sodium hydroxide solution (120 mL) and 30% aqueous hydrogen peroxide (100 mL) were gradually added thereto. The purified aqueous mixture was stirred overnight, followed by two extractions with dichloromethane. The organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated. The residue was purified by chromatography (hexane/ethyl acetate=4:1→2:1→1:1) to obtain the title compound (8.18 g, 85%) as a colorless oil.

Aufarbeitung

  1. extractionfollowed by two extractions with dichloromethane
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (hexane/ethyl acetate=4:1→2:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c497bffb1396404884d34cbebe1e41a4
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735425B2

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