Triphenylphosphine → HCID 178498033, Verbindung

HRID 1095147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095147
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:27]([Si:31]([CH3:41])([CH3:40])[O:32][C@H:33]1[CH2:38][CH2:37][C@H:36](O)[CH2:35][CH2:34]1)([CH3:30])([CH3:29])[CH3:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:12][C@H:36]1[CH2:37][CH2:38][C@@H:33]([O:32][Si:31]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:40])[CH3:41])[CH2:34][CH2:35]1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl esterHCID 178455371HCID 178455371, Verbindung

Produkt 1

HCID 178498033HCID 178498033, VerbindungAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of methyl 5-chloro-2-hydroxybenzoate (2.07 g, 11 mmol) and diisopropyl azodicarboxylate (2.98 g, 14 mmol) (Aldrich) in anhydrous tetrahydrofuran (10 mL) at 0° C. was added a mixture of trans-4-(tert-buyl-dimethyl-silanyloxy)-cyclohexanol (3.2 g, 14 mmol) and triphenylphosphine (3.64 g, 14 mmol) in tetrahydrofuran (40 mL). The reaction mixture was stirred at room temperature for 18 h. The mixture was poured into water, extracted with ethyl acetate (3×). The organic layers were combined, washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (5% EtOAc;hexanes) to give cis-2-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-5-chloro-benzoic acid methyl ester as a yellow oil (Yield 4.0 g, 90%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×)
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (5% EtOAc;hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c1446325c1fe49d1b66f0a0809f49b9d
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134001B2

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