Methanol → 2-(1,6-dimethyl-1H-indol-3-yl)acetonitrile

HRID 442745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442745
CC(C)([O-])C.[K+].CC1C=CC(S([CH2:17][N+:18]#[C-])(=O)=O)=CC=1.[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH3:30])[CH:28]=2)[C:23]([CH:31]=O)=[CH:22]1.CO>COCCOC>[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH3:30])[CH:28]=2)[C:23]([CH2:31][C:17]#[N:18])=[CH:22]1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 161915Tosylmethyl isocyanideHCID 225937461,6-Dimethyl-1H-indole-3-carbaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 537377192-(1,6-dimethyl-1H-indol-3-yl)acetonitrileAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A suspension of potassium tert-butoxide (KOtBu) (2.21 g, 19.7 mm) in DME (30 mL) was cooled to -30° C., and treated with a solution of TosMIC (1.97 g 10.1 mm). After addition was complete, the mixture was further cooled to -60° C., treated with 1,6-dimethyl-1H-indole-3-carboxaldehyde (5.8 mm) in DME(20 mL), and stirred at that temperature for 1.5 hours. Addition of methanol (15 mL) to the cooled solution, was followed by heating to reflux temperature for 15 minutes, and evaporation of the solvent. The residue was treated with H2O (20 mL) containing acetic acid (HOAc) (0.75 mL), then extracted with CH2Cl2 (50 mL×3). The combined organic fractions were extracted with saturated NaHCO3 solution, dried over MgSO4, filtered and evaporated. Purification by flash column chromatography afforded (1,6-dimethyl-1H-indol-3-yl)-acetonitrile (0.86 g, 81%).

Aufarbeitung

  1. additionAfter addition
  2. temperaturethe mixture was further cooled to -60° C.
  3. temperatureby heating
  4. temperatureto reflux temperature for 15 minutes
  5. customevaporation of the solvent
  6. additionThe residue was treated with H2O (20 mL)
  7. additioncontaining acetic acid (HOAc) (0.75 mL)
  8. extractionextracted with CH2Cl2 (50 mL×3)
  9. extractionThe combined organic fractions were extracted with saturated NaHCO3 solution
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated
  13. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-66560d5ecb814ea594ac00655dd06dba
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891901

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