Water → HCID 10607811, compound

HRID 2396831Notes

Reaction equation

HRID 2396831 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][CH: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][CH:14]([OH:15])[CH3:16])[CH:8]=[CH:7]2

Participants

7

Reactant 4

HCID 962WaterHCID 6378Propylene OxideHCID 24758Sodium hydrideHCID 678615-Fluoroindole

Product 1

HCID 10607811HCID 10607811, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.55 g of sodium hydride dispersion in 75 ml of tetrahydrofuran was treated with 2 g of 5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 2.1 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 24 hours and subsequently treated with 5 ml of water. The mixture was diluted with ether, washed three times with 75 ml of water each time and with 70 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 60 g of silica gel with toluene-ethyl acetate (19:1). There were obtained 1.8 g (62%) of (RS)-1-(5-fluoro-indol-1-yl)-propan-2-ol as a yellow oil.

Workup

  1. stirringwas stirred at room temperature for 24 hours
  2. washwashed three times with 75 ml of water each time
  3. dry with materialwith 70 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 60 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-7908756d46c54447b0b70d27bde3b763
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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