Tetrahydrofuran → trans-3-[3-(1-Dodecynyl)phenyl]propen-1-ol
Reaktionsgleichung
[C:1]([C:13]1[CH:14]=[C:15](/[CH:19]=[CH:20]/[C:21](OCC)=[O:22])[CH:16]=[CH:17][CH:18]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+]>C(OCC)(=O)C>[C:1]([C:13]1[CH:14]=[C:15]([CH2:19]/[CH:20]=[CH:21]/[OH:22])[CH:16]=[CH:17][CH:18]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of ethyl trans-3-[3-(1-dodecynyl)phenyl]-2-propenoate (10.0 g) and dry tetrahydrofuran (100 ml) at -78° C. was added diisobutylaluminum hydride (1.5M in toluene) (49 ml) slowly. The reaction mixture was stirred for 20 mins at -78° C., and 25% sodium hydroxide solution (3 ml) was added. The mixture was slowly warmed to room temperature and an additional 25% sodium hydroxide solution (3 ml) was added. The mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was flash chromatographed over silica gel (eluted with ethyl acetate/hexane/1:3). The appropriate fractions were collected and evaporated to afford 7.14 g (81%) of product.
Aufarbeitung
- temperatureThe mixture was slowly warmed to room temperature
- washwashed with water and brine
- customThe organic phase was separated
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated in vacuo
- customchromatographed over silica gel (eluted with ethyl acetate/hexane/1:3)
- customThe appropriate fractions were collected
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-54ef48131f054c729ea7752894c6193d
- Quelldatensatz
- uspto-grants-1996_01
- Patentnummer
- US05488063
Notizen zur Reaktion
Wird geladen…