Reaktionsgleichung
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:15][O:14][C:13](=[O:16])[C:12]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CC(C[AlH]CC(C)C)C.[OH-].[Na+]>ClCCl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8](/[C:11](=[C:12](\[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)/[CH2:13][OH:16])/[CH2:15][OH:14])=[CH:9][CH:10]=1)(=[O:3])=[O:4]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 110 g of 4-(4-methanesulfonyl-phenyl)-3-phenyl-5H-furan-2-one in 1.5 L of dichloromethane stirred at −78° C., 150 mL of DIBAL was added dropwise. The resulting mixture was warmed to room temperature and stirred overnight. The reaction mixture was then cooled to −78° C., and 1.2 L of 1 M aqueous NaOH was added dropwise. After the addition, the resulting mixture was warmed to room temperature and the organic phase was separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined and dried over Na2SO4. 110 g of the titled compound was obtained after evaporation. 1H NMR (acetone-d6, 500 M Hz): δ 7.69 (d, 2 H), 7.36 (d, 2 H), 7.16–7.05 (m, 5 H), 4,66 (d, 2 H), 4.63 (d, 2 H), 4.19 (t, 1 H, OH), 4.17 (t, 1 H. OH), 3.04 (s, 3 H).
Aufarbeitung
- temperatureThe reaction mixture was then cooled to −78° C.
- additionAfter the addition
- temperaturethe resulting mixture was warmed to room temperature
- customthe organic phase was separated
- extractionThe aqueous phase was extracted with dichloromethane
- dry with materialdried over Na2SO4
Quellen und Nachweise
- ORD-Eintrag
- ord-a0d1798d1a4a4937b9d1bbf49333574c
- Quelldatensatz
- uspto-grants-2007_04
- Patentnummer
- US07199154B2
Verknüpfte Notizen
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