Calcium Carbonate → HCID 22506878, Verbindung

HRID 985600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 985600
[OH:1][C:2]1[C:3]([CH3:20])=[C:4]2[C:8](=[C:9]([CH3:15])[C:10]=1[CH2:11][C:12]([CH3:14])=[CH2:13])[N:7]([CH:16]=[O:17])[C:6]([CH3:19])([CH3:18])[CH2:5]2.C(=O)([O-])[O-].[Ca+2].[I:26](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>ClCCl.CO>[I:26][CH2:13][C:12]1([CH3:14])[O:1][C:2]2=[C:3]([CH3:20])[C:4]3[CH2:5][C:6]([CH3:19])([CH3:18])[N:7]([CH:16]=[O:17])[C:8]=3[C:9]([CH3:15])=[C:10]2[CH2:11]1

Komponenten

6

Edukt 3

HCID 10112Calcium CarbonateHCID 22506835HCID 22506835, VerbindungHCID 56924451Trimethylbenzylammonium Dichloroiodate

Produkt 1

HCID 22506878HCID 22506878, VerbindungAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2,3-dihydro-5-hydroxy-2,2,4,7-tetramethyl-6-(2-methyl-2-propenyl)-1H-indole-1-carbaldehyde (1.90 g, 6.95 mmol) in dichloromethane (20 ml) and methanol (10 ml) were added calcium carbonate (0.90 g, 9.0 mmol) and benzyltrimethylammonium dichloroiodate (2.66 g, 7.64 mmol), and stirred for 15 minutes at room temperature. The reaction mixture was filtered and concentrated under reduced pressure. To the residue was added a 5% aqueous solution of sodium hydrogen sulfite (15 ml), and extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine and water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to obtain 2.40 g of the title compound.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added a 5% aqueous solution of sodium hydrogen sulfite (15 ml)
  4. extractionextracted twice with ethyl acetate
  5. washwashed with saturated brine and water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-b357f43d1fad498994784d733f43700e
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06872718B1

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