Sodium hydride → 4-(oxiran-2-ylmethoxy)-1H-indole

HRID 40629

Reaktionsgleichung

Reaktionsgleichung von HRID 40629
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].[N+](C1C=C(S(O[CH2:26][C@@H:27]2[O:29][CH2:28]2)(=O)=O)C=CC=1)([O-])=O>CN(C)C=O.C(OCC)(=O)C.CCCCCCC>[O:29]1[CH2:28][CH:27]1[CH2:26][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 754211H-indol-4-olHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl ester

Produkt 1

HCID 6050154-(oxiran-2-ylmethoxy)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel3×HCID 8900HeptaneLösungsmittel

Versuchsvorschrift

4-hydroxy indole (0.08 g, mmol) was dissolved in dimethylformamide (1.5 mL). Sodium hydride (0.02 g, 0.51 mmol) was slowly added to the reaction mixture followed by addition of (R)-glycidyl 3-nitrobenzene sulfonate (0.132, 0.51 mmol). A red color appeared. After 3 hour the reaction mixture was poured into a separatory funnel and ethyl acetate (100 mL) was added. The organic layer was washed 3 times with a 10% solution of sodium carbonate in water. The aqueous layers were discarded, the organic layer was dried with sodium sulfate and the solvent was removed by reduced pressure to yield crude product. The crude product was dissolved in ethyl acetate, Celite® (approximately 3 grams) was added, followed by removal of the solvent under reduced pressure. The Celite®/reaction mixture was loaded into an Isco solid phase loading cartridge. Flash chromatography was carried out using an Isco Companion automated chromatography system, silica column (4 g), initially holding at 5% ethyl acetate in heptane for 3 column volumes, increasing the ethyl acetate concentration to 60% over 40 column volumes, holding at 60% ethyl acetate for 10 more column volumes to yield the title compound as a residue.

Aufarbeitung

  1. additionAfter 3 hour the reaction mixture was poured into a separatory funnel
  2. washThe organic layer was washed 3 times with a 10% solution of sodium carbonate in water
  3. dry with materialthe organic layer was dried with sodium sulfate
  4. customthe solvent was removed by reduced pressure
  5. customto yield crude product
  6. additionCelite® (approximately 3 grams) was added
  7. customfollowed by removal of the solvent under reduced pressure
  8. customThe Celite®/reaction mixture
  9. temperatureincreasing
  10. concentrationthe ethyl acetate concentration to 60% over 40 column volumes

Quellen und Nachweise

ORD-Eintrag
ord-84fa0ae3d8e145d5992da9e839ad5898
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530475B2

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