Triphenylphosphine → HCID 60128036, Verbindung

HRID 350993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350993
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][O:12][C:13](=[O:18])[C@@H:14]([CH3:17])[CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:18])[C@@H:14]([CH3:17])[CH2:15][O:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 10192563methyl (2S)-3-hydroxy-2-methylpropanoate

Produkt 1

HCID 60128036HCID 60128036, VerbindungAusbeute 8,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-fluoro-4-hydroxybenzonitrile (1.0 g, 7.3 mmol), (S)-3-hydroxy-2-methyl-propionic acid methyl ester (0.8 mL, 7.3 mmol) and triphenylphosphine (2.3 g, 8.8 mmol) at room temperature, diethyl azodicarboxylate (1.4 mL, 8.8 mmol) was added dropwise. The mixture was stirred at room temperature overnight, diluted with ethyl acetate and washed successively with dilute aqueous sodium hydroxide, dilute aqueous hydrochloric acid, brine, and dried (MgSO4). Solvents were stripped in vacuo. The resulting oil was washed with diethyl ether and the precipitate was filtered off. The mother liquor was adsorbed onto silica gel and the product purified by flash column chromatography (40% ethyl acetate/hexane), affording 0.14 g of a yellow oil (8% yield).

Aufarbeitung

  1. washwashed successively with dilute aqueous sodium hydroxide, dilute aqueous hydrochloric acid, brine
  2. dry with materialdried (MgSO4)
  3. washThe resulting oil was washed with diethyl ether
  4. filtrationthe precipitate was filtered off
  5. customthe product purified by flash column chromatography (40% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4c9fa0b8cba6460498c48c0c63c8ad7d
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183293B2

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