Water → HCID 10488020, compound

HRID 2396840Notes

Reaction equation

HRID 2396840 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.[CH3:13][CH:14]1[CH2:16][O:15]1.O>O1CCCC1.CCOCC>[F:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][CH:14]([OH:15])[CH3:16])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6378Propylene OxideHCID 24758Sodium hydrideHCID 3512786-Fluoroindole

Product 1

HCID 10488020HCID 10488020, compoundYield 79.3%

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 0.97 g of 6-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 1 ml of (RS)-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 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 1.1 g (79.3%) of (RS)-1-(6-fluoro-indol-1-yl)-propan-2-ol as a colourless oil.

Workup

  1. stirringwas stirred at room temperature for 48 hours
  2. washwashed twice with 90 ml of water and with 50 ml of saturated sodium chloride solution
  3. dry with materialthe 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-eaf936c7e12e4354811961fd9a0a9416
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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