Water → HCID 53943940, compound

HRID 2396857Notes

Reaction equation

HRID 2396857 reaction equation
[H-].[Na+].[CH:3]([C:6]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)([CH3:5])[CH3:4].[CH3:16][C@@H:17]1[CH2:19][O:18]1.O>O1CCCC1.CCOCC>[CH:3]([C:6]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[CH2:16][C@H:17]([OH:18])[CH3:19])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 146261(R)-1,2-EpoxypropaneHCID 18986336HCID 18986336, compound

Product 1

HCID 53943940HCID 53943940, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.16 g of sodium hydride dispersion in 22 ml of tetrahydrofuran was treated with 0.38 g of 4-isopropyl-5-fluoroindole at 0° and stirred at this temperature for I hour. After the addition of 0.6 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 120 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 25 g of silica gel with toluene-ethyl acetate (19:1). 0.41 g (81%) of (R)-1-(4-isopropyl-5-fluoro-indol-1-yl)-propan-2-ol was obtained as a yellow oil.

Workup

  1. stirringwas stirred at room temperature for 120 hours
  2. washwashed with water and 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 25 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-04766d6e5d8647779533387736d7bebe
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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