Sodium Hydroxide → 7-Methyl-2,3-dihydro-1H-indole

HRID 1275647

Reaktionsgleichung

Reaktionsgleichung von HRID 1275647
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 702757-MethylindoleHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 123777887-Methyl-2,3-dihydro-1H-indoleAusbeute 111,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 7-methylindole (10.27 g, 78.3 mmol) in glacial acetic acid (50 mL) is added sodium cyanoborohydride (6.33 g, 100.7 mmol) portionwise over a 5 minute period. The reaction solution is allowed to stir for 1 hour. The solution is diluted with water (500 mL) and basified with 50% sodium hydroxide solution. The basic solution is extracted with three 250 mL portions of diethyl ether. The organic fractions are combined, dried over anhydrous potassium carbonate, filtered and evaporated to give a pink oil. The oil is purified by silica gel column chromatography using 20% ethyl acetate/hexanes as eluent to give 11.63 g of 2,3-dihydro-7-methylindole as a colorless oil (94% yield).

Aufarbeitung

  1. extractionThe basic solution is extracted with three 250 mL portions of diethyl ether
  2. dry with materialdried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a pink oil
  6. customThe oil is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6311792080f14d9093bb90b63962aede
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162818

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