Water → HCID 10655269, compound

HRID 2396850Notes

Reaction equation

HRID 2396850 reaction equation
[H-].[Na+].[CH3:3][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>[CH3:3][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 119785-MethylindoleHCID 24758Sodium hydride

Product 1

HCID 10655269HCID 10655269, compoundYield 62.7%

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 of 5-methylindole 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 water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 30 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.86 g (62.7%) of (RS)-1-(5-methyl-indol-1-yl)-propan-2-ol as a yellow oil.

Workup

  1. stirringwas stirred at room temperature for 48 hours
  2. washwashed with water and with 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 30 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-589cfa4b8f114ae6a69985753c42057a
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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