3,5-Dinitrobenzoic acid → HCID 86749722, Verbindung

HRID 279161

Reaktionsgleichung

Reaktionsgleichung von HRID 279161
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C@H:11]([OH:13])[CH3:12])[CH2:10][O:9]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:33]([C:36]1[CH:37]=[C:38]([CH:42]=[C:43]([N+:45]([O-:47])=[O:46])[CH:44]=1)[C:39](O)=[O:40])([O-:35])=[O:34].N(C(OCC)=O)=NC(OCC)=O.C(OC(C)C)(C)C>O1CCCC1.O.C(OCC)(=O)C>[N+:33]([C:36]1[CH:37]=[C:38]([CH:42]=[C:43]([N+:45]([O-:47])=[O:46])[CH:44]=1)[C:39]([O:13][C@H:11]([C@@:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:10][O:9]1)[CH3:12])=[O:40])([O-:35])=[O:34]

Komponenten

9

Edukt 5

HCID 74333,5-Dinitrobenzoic acidHCID 7914Diisopropyl EtherHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86749723HCID 86749723, Verbindung

Produkt 1

HCID 86749722HCID 86749722, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(2-Fluorophenyl)-2-[(l1R)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxyethyl] oxirane (synthesized by the method described in EP0548553A) was converted into (1R)-1-[2-(2-fluorophenyl)-2-oxiranyl]ethanol by the method described in Reference Example 1. To an ice-cooled solution of this compound (34.77 g) in tetrahydrofuran (600 ml) were added triphenylphosphine (127.21 g), 3,5-dinitrobenzoic acid (102.88 g) and diethyl azodicarboxylate (84.47 g). The mixture was stirred at room temperature for 7 hours under an argon atmosphere, and then ethyl acetate (600 ml), diisopropyl ether (100 ml) and water (800 ml) were added. The separated aqueous layer was extracted with ethyl acetate (600 ml, 400 ml). The organic layers were combined, washed with water and a saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=5/1) and recrystallized from ethyl acetate to give [(1S)-1-[(2R)-2-(2-fluorophenyl)-2-oxiranyl]ethyl] 3,5-dinitrobenzoate (23.15 g) as colorless needles.

Aufarbeitung

  1. extractionThe separated aqueous layer was extracted with ethyl acetate (600 ml, 400 ml)
  2. washwashed with water
  3. dry with materiala saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=5/1)
  6. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-04f57a965b214a38bbfbe8ba3893900b
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362206B1

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