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

HRID 51016Notes

Reaction equation

HRID 51016 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8c0ed42b13a54ccca6b12550ad106d06
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

Loading…