Water → (1-methyl-1H-indol-2-yl)methanol

HRID 1599265

Reaktionsgleichung

Reaktionsgleichung von HRID 1599265
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11](OC)=[O:12].[BH4-].[Li+].O>O1CCCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][OH:12]

Komponenten

5

Edukt 3

HCID 962WaterHCID 258548methyl 1-methyl-1H-indole-2-carboxylateHCID 4148881Lithium borohydride

Produkt 1

HCID 295652(1-methyl-1H-indol-2-yl)methanolAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 5.05 g of methyl 1-methylindole-2-carboxylate (prepared as described in Preparation 22) in 20 ml of anhydrous tetrahydrofuran was added dropwise to a mixture of 1.85 g of lithium borohydride and 80 ml of anhydrous tetrahydrofuran, and the resulting mixture was heated under reflux for 4 hours. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 4.30 g of the title compound, melting at 92.8°-95.2° C.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1e2486bf5699489daa77858c3b217085
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739345

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