Ethyl Acetate → Methyl 4-(2-methylindol-3-yl)butyrate

HRID 1974558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1974558
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11](=O)[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(OCC)(=O)C>O1CCCC1.[Cl-].[Na+].O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 730054Methyl 4-(2-methylindol-3-yl)-4-oxobutyrate

Produkt 1

HCID 10609557Methyl 4-(2-methylindol-3-yl)butyrateAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of methyl 4-(2-methylindol-3-yl)-4-oxobutyrate (2.0 g) in tetrahydrofuran (50 ml) was added a 1M solution of boran in tetrahydrofuran (16.5 ml) at 0° C. After stirred at 0° C. for 30 minutes, the mixture was poured into a mixture of ethyl acetate and brine. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of solvent, the residue was purified by column chromatography on silica gel (50 g) eluting with chloroform to give methyl 4-(2-methylindol-3-yl)butyrate (1.67 g) as a yellow oil.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of solvent
  5. customthe residue was purified by column chromatography on silica gel (50 g)
  6. washeluting with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-7cd8598994e745ee9b96caf2229f6eba
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05283251

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