5-Methoxyindole-3-carbaldehyde → (5-methoxy-1H-indol-3-yl)methanol

HRID 384868

Reaktionsgleichung

Reaktionsgleichung von HRID 384868
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]2[NH:11][CH:12]=[C:13]([CH:14]=[O:15])[C:7]=2[CH:6]=1>CO.C1COCC1.O.C(=O)([O-])[O-].[K+].[K+]>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][CH:10]=1)[NH:11][CH:12]=[C:13]2[CH2:14][OH:15]

Komponenten

7

Edukt 2

HCID 827585-Methoxyindole-3-carbaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 4255293(5-methoxy-1H-indol-3-yl)methanolAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

To a solution of sodium borohydride (2 grams, 0.05 mol) in methanol (15 ml), a solution of 5-methoxy-1H-indol-3-carboxaldehyde 2 (1 gram, 0.006 mol) dissolved in THF (20 ml) and methanol (15 ml) were combined and stirred at ambient temperature for 16 hours. The reaction was diluted with water and potassium carbonate (to saturation) and stirred to quench unreacted sodium borohydride. Diethyl ether was used to extract the product from the quenched solution. Following layers separation, the aqueous layer was further extracted (2×) with diethyl ether. The combined organic pats were dried over sodium sulfate and evaporated to dryness to yield a light colored solid 141 (736 mg, 70%).

Aufarbeitung

  1. stirringstirred
  2. customto quench unreacted sodium borohydride
  3. extractionto extract the product from the quenched solution
  4. customFollowing layers separation
  5. extractionthe aqueous layer was further extracted (2×) with diethyl ether
  6. dry with materialThe combined organic pats were dried over sodium sulfate
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d912c6b39a454f8fa6e28415445f49d8
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367828B2

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