Acetic Anhydride → HCID 11725738, Verbindung

HRID 1376193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376193
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH:19]=[O:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]([Mg]Cl)=[CH2:22].[C:25](OC(=O)C)(=[O:27])[CH3:26]>O1CCCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH:19]([O:20][C:25](=[O:27])[CH3:26])[CH:21]=[CH2:22])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 27762231-(Phenylsulfonyl)-1H-indole-2-carbaldehydeHCID 178461836HCID 178461836, Verbindung

Produkt 1

HCID 11725738HCID 11725738, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2.9 g (10 mmol) of 1-benzenesulfonyl-1H-indole-2-carbaldehyde (synthesized analogous to M. G. Saulnier, G. W. Gordon, J.Org.Chem.; 47; 5; 1982, 757–761) in 10 ml of tetrahydrofuran was added 6.5 ml of vinylmagnesium chloride 1.7 M solution in THF at −20° C. within 1 h. The temperature increased to 0° C. within 30 min and kept at this temperature for 20 min. To the suspension 1.3 ml acetic anhydride (14 mmol was added at 0° C. within 15 min. The cooling bath was removed and after stirring for 1 h at 20° C. 10 ml water was added at 10–15° C. The mixture was stirred for an additional 1 h at 20° C. The phases were separated, and the aqueous phase was extracted with 20 ml of ethyl acetate. The combined organic phases were washed with 20 ml of brine, dried on sodium sulfate and rotary evaporated (35° C., 12 mbar). The crude material was purified by liquid chromatography (eluent isohexane/ethyl acetate 9:1).

Aufarbeitung

  1. customThe cooling bath was removed
  2. addition10 ml water was added at 10–15° C
  3. stirringThe mixture was stirred for an additional 1 h at 20° C
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with 20 ml of ethyl acetate
  6. washThe combined organic phases were washed with 20 ml of brine
  7. customdried on sodium sulfate
  8. customrotary evaporated (35° C., 12 mbar)
  9. customThe crude material was purified by liquid chromatography (eluent isohexane/ethyl acetate 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-0b0fdbb3f5a1423598063a937ff741c4
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169935B2

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