7-Methyl-1,4-dioxaspiro[4.5]decan-8-one → cis-7-Methyl-1,4-dioxa-spiro[4.5]decan-8-ol
Reaktionsgleichung
[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.[Li+].[B-](CC)(CC)CC>C1COCC1>[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]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Dissolve 7-methyl-1,4-dioxa-spiro[4.5]decan-8-one (11.45 g, 67.28 mmol) in THF (300 mL) and cool the solution to 0° C. under N2. Add super-hydride (74.0 mL, 74.0 mmol, 1 M in THF) and stir the reaction mixture overnight. Add water (200 mL), and extract the aqueous layer with dichloromethane (3×300 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 30-50% of EtOAc/Hexane) to give cis-7-Methyl-1,4-dioxa-spiro[4.5]decan-8-ol.
Aufarbeitung
- extractionAdd water (200 mL), and extract the aqueous layer with dichloromethane (3×300 mL)
- dry with materialCombine the organic layers and dry with Na2SO4
- filtrationfilter
- concentrationconcentrate
- custompurify by flash column chromatography (silica gel, 30-50% of EtOAc/Hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-fb1a4ae12c1f48c1bcf04ea7d8bb5b30
- Quelldatensatz
- uspto-grants-2010_05
- Patentnummer
- US07713979B2
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