Tetrahydrofuran → 3-(6-fluoro-1H-indol-3-yl)propan-1-ol

HRID 51016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51016
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7](CCC(O)=O)[NH:8]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:22]1C[O:25][CH2:24][CH2:23]1>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 227354403-(6-Fluoroindolyl)propionic acid

Produkt 1

HCID 115212333-(6-fluoro-1H-indol-3-yl)propan-1-olAusbeute 65 %

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 3-(6-fluoroindolyl)propionic acid (235 mg, 1.13 mmol) in THF (5.3 mL) was added LiAlH4 (86 mg, 2.26 mmol) slowly at 0° C. under N2. The reaction mixture was warmed to 20° C. and stirred for 15 h. The reaction was quenched by addition of H2O (0.5 mL) and diluted with EtOAc. The resulting solution was dried over MgSO4, filtered through Celite and concentrated in vacuo. The residue was chromatographed to give 6-fluoro-3-(3-hydroxypropyl)indole (142 mg, 65%) as a colorless oil.

Aufarbeitung

  1. customThe reaction was quenched by addition of H2O (0.5 mL)
  2. additiondiluted with EtOAc
  3. dry with materialThe resulting solution was dried over MgSO4
  4. filtrationfiltered through Celite
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-8c0ed42b13a54ccca6b12550ad106d06
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

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