Triethylamine → HCID 178431083, Verbindung

HRID 468637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 468637
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[O:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([CH2:28][OH:29])[CH2:24][CH2:23]1.[CH3:30][C:31]1([CH3:45])[C:35]([CH3:37])([CH3:36])[O:34][B:33]([C:38]2[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=2)[O:32]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1.O>[CH3:36][C:35]1([CH3:37])[C:31]([CH3:30])([CH3:45])[O:32][B:33]([C:38]2[CH:43]=[CH:42][C:41]([O:29][CH2:28][C@H:25]3[CH2:26][CH2:27][C@H:22]([O:21][CH:16]4[CH2:17][CH2:18][CH2:19][CH2:20][O:15]4)[CH2:23][CH2:24]3)=[CH:40][CH:39]=2)[O:34]1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178520985HCID 178520985, Verbindung

Produkt 1

HCID 178431083HCID 178431083, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diisopropyl azodicarboxylate (2.1 mL, 10.5 mmol) was added to a solution of [trans-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]methanol (2.05 g, 9.57 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (2.3 g, 10.7 mmol), triphenylphosphine (2.76 g, 10.5 mmol), and triethylamine (1.5 mL, 10.5 mmol) in THF (150 mL) at 0° C. The reaction was allowed to warm to it and stirred overnight. Water (200 mL) was added and the reaction was extracted with EtOAc (600 mL). The organics were washed with 1 M aq NaOH (4×100 mL), brine, then dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified via flash chromatography using an eluent of 20% EtOAc in hexanes to afford the title compound as a white solid (1.9 g, 48%). MS (APCI) m/z 417.3 (M+1).

Aufarbeitung

  1. temperatureto warm to it
  2. extractionthe reaction was extracted with EtOAc (600 mL)
  3. washThe organics were washed with 1 M aq NaOH (4×100 mL), brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-97d66b569edf43d8933a4cb357eda442
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08624034B2

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