Reaktionsgleichung
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C:11]#[C:12][CH2:13][OH:14].I[CH2:16][CH3:17]>CN(C=O)C>[CH3:8][O:3][C:4]([CH3:5])=[O:9].[CH3:4][CH2:5][CH2:6][CH2:7][CH2:16][CH3:17].[CH2:16]([O:14][CH2:13][C:12]#[C:11][CH2:10][O:9][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][O:3]1)[CH3:17]Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
An oven dried 500 ml RBF was charged with NaH (60% in mineral oil) (1.41 g, 35.3 mmol) and suspended in DMF (100 mL). The mixture was cooled to 0° C. and 4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol (prepared in accordance with the procedures of Tamaru et al., Bull. Chem. Soc. Jpn., 1995, 1689-1705) (6.0 g, 35.3 mmol) was added. The reaction mixture was allowed to reach room temperature and stirred for one hour. To the mixture was added iodoethane (20.8 g, 133 mmol). The reaction mixture was stirred for 3.5 hours at room temperature before being quenched with ice/H2O and extracted with MeOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (1-20% MeOAc/hexane) provided 4.71 g of 2-(4-ethoxy-but-2-ynyloxy)-tetrahydro-pyran as a clear oil.
Aufarbeitung
- customAn oven dried 500 ml RBF
- addition, 1995, 1689-1705) (6.0 g, 35.3 mmol) was added
- customto reach room temperature
- stirringThe reaction mixture was stirred for 3.5 hours at room temperature
- custombefore being quenched with ice/H2O
- extractionextracted with MeOAc
- washThe organic phase was washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-fd436759d4e74f2f98770a0ccab266a0
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08642603B2
Verknüpfte Notizen
Wird geladen…