Sodium Hydroxide → methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylate

HRID 1165178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1165178
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:14])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[BH4-].[Na+].[OH-].[Na+]>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[CH3:14])=[O:4]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 258548methyl 1-methyl-1H-indole-2-carboxylateHCID 4311764Sodium borohydride2×

Produkt 1

HCID 12658762methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of methyl-1-methylindole-carboxylate* (6.0 g) in trifluoroacetic acid (50 ml) is cooled in an ice bath as sodium borohydride pellets (6.0 g) are added slowly, keeping the temperature below 10° C. The slurry is allowed to rise to room temperature and then stirred overnight. The unreacted sodium borohydride is decomposed with 50% sodium hydroxide and the mixture is extracted several times with ether. The extracts are washed with saturated sodium chloride solution, dried over sodium sulfate, and evaporated to dryness to obtain an orange oil. This is distilled in a kuegelrohr (b.p.=128-150/0.2 mm) to yield colorless liquid, methyl-2, 3-dihydro-1-methylindole-carboxylate.

Aufarbeitung

  1. additionare added slowly
  2. customthe temperature below 10° C
  3. customto rise to room temperature
  4. extractionthe mixture is extracted several times with ether
  5. washThe extracts are washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customto obtain an orange oil
  9. distillationThis is distilled in a kuegelrohr (b.p.=128-150/0.2 mm)

Quellen und Nachweise

ORD-Eintrag
ord-f208ba7f029746cc9642f2d54ab1a778
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04908376

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