Benzyl Bromide → 1-benzyl-1H-indole-3-carbaldehyde

HRID 1392262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392262
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[CH2:14]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydride

Produkt 1

HCID 2621041-benzyl-1H-indole-3-carbaldehydeAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1H-indole-3-carbaldehyde (25.0g, 172 mmol) in tetrahydrofuran (500 mL) cooled to 0° C. with an ice-bath and under an inert atmosphere was slowly added sodium hydride (4.96 g, 207 mmol), such that the temperature of the mixture remained less that 5° C. After complete addition, the mixture was allowed to stir at 0° C. for 15 minutes. To the mixture was added benzyl bromide (35.4 g, 207 mmol). The ice bath was removed and the mixture was allowed to warm to room temperature over 1.5 hours. The mixture was then partitioned between brine and ethyl acetate. The layers were separated and the aqueous layer was extracted with two additional portions of ethyl acetate. The combined organics were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting red solids were dissolved in methylene chloride and the solution was filtered through a plug of silica gel. The filtrate was concentrated under reduced pressure until a precipitate began to form. The product was crystallized out of the solution by the addition of an eight-fold volume of hexane. The red-tinted solid was isolated by vacuum filtration, and the process was repeated one additional time to give 1-benzyl-1H-indole-3-carbaldehyde (38.8 g, 96%) as an off-white powder. 1H NMR (400 MHz, CDCl3); δ 9.98 (s, 1H), 8.32 (m, 1H), 7.71 (s, 1H), 7.34 (m, 6H), 7.18 (m, 2H), 5.36 (s, 2H).

Aufarbeitung

  1. customremained less that 5° C
  2. additionAfter complete addition
  3. customThe ice bath was removed
  4. temperatureto warm to room temperature over 1.5 hours
  5. customThe mixture was then partitioned between brine and ethyl acetate
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with two additional portions of ethyl acetate
  8. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. dissolutionThe resulting red solids were dissolved in methylene chloride
  12. filtrationthe solution was filtered through a plug of silica gel
  13. concentrationThe filtrate was concentrated under reduced pressure until a precipitate
  14. customto form
  15. customThe product was crystallized out of the solution by the addition of an eight-fold volume of hexane
  16. customThe red-tinted solid was isolated by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-8208e2a9d443483bb61480f3c2adf4ee
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342039B2

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