Reaktionsgleichung
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[C@@H:49]1[CH2:53][CH2:52][O:51][CH2:50]1.Cl>>[CH3:13][C:7]1([CH3:14])[CH2:6][C:5]2[C:10](=[CH:11][C:2]([O:1][C@H:49]3[CH2:53][CH2:52][O:51][CH2:50]3)=[CH:3][CH:4]=2)[C:9](=[O:12])[CH2:8]1Komponenten
6
Versuchsvorschrift
7-Hydroxy-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one (0.95 g, 4.99 mmol) was dissolved in 30 ml DCMand triphenylphosphine (1.96 g, 7.49 mmol) and diisopropyl azodicarboxylate (1.23 ml, 6.24 mmol) and (r)-(−)-3-hydroxytetrahydrofuran (0.600 ml, 7.49 mmol) was added. The mixture was stirred over night. 0.5M HCl (aq.) was added and the mixture was extracted 3 times with EtOAc. Glass col. Chrom. (5-30% EtOAc in Hex.) provided (S)-3,3-dimethyl-7-(tetrahydrofuran-3-yloxy)-3,4-dihydronaphthalen-1(2H)-one as a yellow oil. MS m/z: 261.1 (M+1).
Aufarbeitung
- additionwas added
- extractionthe mixture was extracted 3 times with EtOAc
Quellen und Nachweise
- ORD-Eintrag
- ord-2feb82fb478d44088ec95315aa0396ce
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07745484B2
Verknüpfte Notizen
Wird geladen…