Reaktionsgleichung
[CH:1](/O)=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Br-].[Na+].[C:13](=[O:16])(O)[O-:14].[Na+]>ClCCl.O.[O-]Cl.[Na+]>[CH2:5]([C@H:6]1[CH2:7][C@H:8]1[CH2:9][C:13]([OH:14])=[O:16])[CH2:4][CH2:3][CH2:2][CH3:1]Komponenten
Versuchsvorschrift
Cis-nonen-1-ol (10.0 g) is subjected to the cyclopropanation conditions as described in the preparation of Example 52. The resulting residue is taken up in 100 mL of dichloromethane at 0° C., followed by the addition of 800 mg of sodium bromide in 2 mL of water and 150 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical. To this mixture is added 1.50 g of Aliquot 336 followed by the dropwise addition of 9.2 g of sodium bicarbonate in 230 mL of 5% NaOCl. The aqueous phase is made basic, separated from the organic phase and acidified with concentrated HCl, and then extracted three times with dichloromethane. The combined organic layers are washed with water, dried over MgSO4, and concentrated in vacuo to give cis-2-(2'-pentylcyclopropyl) acetic acid.
Aufarbeitung
- customas described in the preparation of Example 52
- additionTo this mixture is added 1.50 g of Aliquot 336
- customseparated from the organic phase
- extractionextracted three times with dichloromethane
- washThe combined organic layers are washed with water
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-fbd4fcdd0c3e4f2bac86c60e0c45fa3b
- Quelldatensatz
- uspto-grants-1997_10
- Patentnummer
- US05679801
Verknüpfte Notizen
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