Triphenylphosphine → (S)-3-(4-bromo-2-fluoro-5-methylphenoxy)dihydrofuran-2(3H)-one
Reaktionsgleichung
[OH:1][C@@H:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:27][C:28]1[C:33]([CH3:34])=[CH:32][C:31](O)=[C:30]([F:36])[CH:29]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1(C)C=CC=CC=1>[Br:27][C:28]1[C:33]([CH3:34])=[CH:32][C:31]([O:1][C@H:2]2[CH2:6][CH2:5][O:4][C:3]2=[O:7])=[C:30]([F:36])[CH:29]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
(R)-3-hydroxydihydrofuran-2(3H)-one (2.0 g, 20 mmol) was suspended in Toluene (150 mL) and triphenylphosphine (6.2 g, 24 mmol) and 4-bromo-2-fluoro-5-methylphenol (4.8 g, 24 mmol) were added and cooled to 0° C. The solution was degassed with nitrogen bubble for 10 minutes. Di-tert-butyl diazene-1,2-dicarboxylate (5.4 g, 24 mmol) was dissolved in toluene (40 mL) and added to the reaction over 5 minutes. The reaction was allowed to slowly warm to ambient temperature overnight. The toluene was removed and the oily residue was purified over silica gel (20 to 40% EtOAc in hexanes) to afford (S)-3-(4-bromo-2-fluoro-5-methylphenoxy)dihydrofuran-2(3H)-one (2.9 g, 10 mmol, 51% yield).
Aufarbeitung
- customThe solution was degassed with nitrogen
- custombubble for 10 minutes
- additionadded to the reaction over 5 minutes
- temperatureto slowly warm to ambient temperature overnight
- customThe toluene was removed
- customthe oily residue was purified over silica gel (20 to 40% EtOAc in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-c624c1c8618f471d8969019eb9540783
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08754226B2
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