Triphenylphosphine → (2R)-2-[(5-Methoxy-2-nitrophenoxy)methyl]oxirane

HRID 270128

Reaktionsgleichung

Reaktionsgleichung von HRID 270128
[O:1]1[CH2:3][C@@H:2]1[CH2:4][OH:5].[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12](O)[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:10]([CH:9]=1)[O:5][CH2:4][C@H:2]1[CH2:3][O:1]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 2196355-Methoxy-2-nitrophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6973630(-)-Glycidol

Produkt 1

HCID 86601492(2R)-2-[(5-Methoxy-2-nitrophenoxy)methyl]oxiraneAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of (2S)-oxiran-2-ylmethanol (296.3 mg, 4.0 mmol), 5-methoxy-2-nitrophenol (676.6 mg, 4.0 mmol) and triphenyl phosphine (1.05 g, 4.0 mmol) in THF (10 mL) was added diethyl azodicarboxylate (DEAD, 704.6 mg, 4.0 mmol) in THF (5 mL) dropwise at room temperature. After addition was completed the reaction mixture was stirred at room temperature overnight. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (040% ethyl acetate in petroleum spirit) to give the subtitled compound (650 mg).

Aufarbeitung

  1. additionAfter addition
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by silica gel flash chromatography (040% ethyl acetate in petroleum spirit)

Quellen und Nachweise

ORD-Eintrag
ord-a161776fb2e24e1792f765b9ca986115
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449475B2

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