Reaktionsgleichung
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:13][C@H:12]([OH:14])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:13][C@H:12]([O:14][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
6
Versuchsvorschrift
To a solution of cis-3-(benzyloxymethyl)cyclobutanol (Albany Molecular, 1.0 g, 5.2 mmol) in CH2Cl2 (20 mL) was added imidazole (0.71 g, 10.4 mmol), DMAP (64 mg, 0.52 mmol) and tert-butyldimethylsilylchloride (TBSCl) (1.6 g, 10.4 mmol). This mixture was stirred at ambient temperature for 16 h, quenched with saturated, aqueous NH4Cl (5 mL) and diluted with EtOAc (10 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3×5 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 50% hexanes/EtOAc) to give the title compound (1.15 g, 3.8 mmol, 72% yield). MS (DCI/NH3) m/z 307 (M+H)+.
Aufarbeitung
- customquenched with saturated, aqueous NH4Cl (5 mL)
- additiondiluted with EtOAc (10 mL)
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (3×5 mL)
- dry with materialThe combined organics were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- custompurified via column chromatography (SiO2, 50% hexanes/EtOAc)
Quellen und Nachweise
- ORD-Eintrag
- ord-f5f9a21780be44ee94d657912589e32e
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08492371B2
Verknüpfte Notizen
Wird geladen…