Triphenylphosphine → (R)-2-(4-Cyano-3-fluoro-phenoxy)-propionic Acid Methyl Ester

HRID 350977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350977
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:11]([O:16][CH3:17])(=[O:15])[C@H:12]([CH3:14])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>[CH3:17][O:16][C:11](=[O:15])[C@H:12]([O:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)[CH3:14]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 94386methyl (S)-lactateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27346752-Fluoro-4-hydroxybenzonitrile

Produkt 1

HCID 60128060(R)-2-(4-Cyano-3-fluoro-phenoxy)-propionic Acid Methyl EsterAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-fluoro-4-hydroxybenzonitrile (0.2 g, 1.5 mmol), methyl (S)-(−)-lactate (0.14 mL, 1.5 mmol) and triphenylphosphine (1.15 g, 4.4 mmol) at room temperature, diethyl azodicarboxylate (0.67 mL, 4.4 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 (Na2SO4). 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 (20% dichloromethane/hexane), affording 0.12 g of a pink oil (36% yield).

Aufarbeitung

  1. washwashed successively with dilute aqueous sodium hydroxide, dilute aqueous hydrochloric acid, brine
  2. dry with materialdried (Na2SO4)
  3. washThe resulting oil was washed with diethyl ether
  4. filtrationthe precipitate was filtered off
  5. customthe product purified by flash column chromatography (20% dichloromethane/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-120dcfea887341f5bb3b2eba2221a15e
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183293B2

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