Dimethylformamide → HCID 68002053, Verbindung
Reaktionsgleichung
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].CN(C=O)C.Br[CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][CH:22]2[CH2:25][CH:20]1[C:21]2([CH3:27])[CH3:26]>>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH:22]3[CH2:25][CH:20]2[C:21]3([CH3:26])[CH3:27])=[CH:4][CH:3]=1Komponenten
Versuchsvorschrift
To a stirred suspension of 4-iodophenol (0.5 g; 2.27 mmol) and 60% NaH (0.16 g, 2.3 mmol) in anhydrous DMF (5 ml) 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane (0.5 g, 2.2 mmol) was added the and mixture was stirred for 3 h at room temperature. After addition of more of 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane (0.2 g) the mixture was stirred for additional 2 h, quenched with NH4Cl solution and diluted to 20 ml with EtOAc. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.61 g, 73%), as a colourless paste. 1H-NMR (CDCl3) 7.51 (d, 2H, J=8.91 Hz); 6.64 (d, 2H, J=8.88 Hz); 3.88 (t, 2H, J=3.21 Hz); 2.34-1.84 (m, 10H); 1.17 (s, 3H); 1.01 (s, 3H).
Aufarbeitung
- additionwas added the and mixture
- stirringwas stirred for additional 2 h
- customquenched with NH4Cl solution
- additiondiluted to 20 ml with EtOAc
- customThe organic layer was separated
- dry with materialdried over MgSO4
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- customthe residue was purified by FCC (SiO2, hexane/EtOAc)
Quellen und Nachweise
- ORD-Eintrag
- ord-1598983820a5444ca432cfc2b84381d2
- Quelldatensatz
- uspto-grants-2015_11
- Patentnummer
- US09193716B2
Notizen zur Reaktion
Wird geladen…