Water → HCID 54045710, compound

HRID 2396834Notes

Reaction equation

HRID 2396834 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH3:13][C@@H:14]1[CH2:16][O:15]1.O>O1CCCC1.CCOCC>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C@H:14]([OH:15])[CH3:16])[CH:8]=[CH:7]2

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 678615-FluoroindoleHCID 146261(R)-1,2-Epoxypropane

Product 1

HCID 54045710HCID 54045710, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.26 g of sodium hydride dispersion in 35 ml of tetrahydrofuran was treated with 0.95 g (7 mmol) of 5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 1 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with 7 ml of water. The mixture was diluted with 180 ml of ether, washed twice with 90 ml of water each time and with 50 ml of saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 28 g of silica gel with toluene-ethyl acetate (19:1). There were obtained 1.09 g (80%) of (R)-1-(5-fluoro-indol-1-yl)-propan-2-ol as a light brown oil.

Workup

  1. stirringwas stirred at room temperature for 48 hours
  2. washwashed twice with 90 ml of water each time
  3. dry with materialwith 50 ml of saturated sodium chloride solution and the organic phase was dried over sodium sulfate
  4. customAfter removal of the solvent the residue
  5. customwas chromatographed over 28 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-06dfc3875edf4b1b80173b1af87cb14b
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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