Water → 3-Buten-2-ol, 1-(triphenylmethoxy)-, (2S)-
Reaktionsgleichung
[Li][CH2:2]CCC.[I-].C[S+](C)C.[CH2:11]([O:15][C:16](C1C=CC=CC=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:12]1[O:14][CH2:13]1.O.[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C1COCC1>[C:16]([O:15][CH2:11][C@@H:12]([OH:14])[CH:13]=[CH2:2])([C:38]1[CH:37]=[CH:36][CH:41]=[CH:40][CH:39]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1Komponenten
7
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
A solution of n-BuLi in hexane (2.6 M; 182 mL) was added dropwise to a solution of trimethylsulfonium iodide (96.8 g) in THF (800 mL) at −30° C. After stirring at −20° C. for 20 minutes, (S)-trityl glycidyl ether (50.0 g) was added at the same temperature, and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (52.0 g).
Aufarbeitung
- stirringthe mixture was stirred at room temperature for 30 minutes
- extractionfollowed by extraction with diethyl ether
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customThe insoluble matter was separated by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-2bd5a171319946ffab37adcf7fa6bb23
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08158620B2
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