Water → HCID 18986325, compound

HRID 2396855Notes

Reaction equation

HRID 2396855 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH3:13])=[CH:7]2.[CH3:14][CH:15]1[CH2:17][O:16]1.O>O1CCCC1.CCOCC>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:14][CH:15]([OH:16])[CH3:17])[C:8]([CH3:13])=[CH:7]2

Participants

7

Reactant 4

HCID 962WaterHCID 6378Propylene OxideHCID 24758Sodium hydrideHCID 706365-Chloro-2-methylindole

Product 1

HCID 18986325HCID 18986325, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 75 ml of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.33 g of 5-chloro-2-methylindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.28 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 13 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.27 g (61.7%) of (RS)-1-(5-chloro-2-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 13 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-0bc93be908a24157ac418db388624d10
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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