Water → HCID 10798475, compound

HRID 2396830Notes

Reaction equation

HRID 2396830 reaction equation
[H-].[Na+].[Cl: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>[Cl: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 871105-Chloroindole

Product 1

HCID 10798475HCID 10798475, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.4 g of sodium hydride dispersion in 60 ml of tetrahydrofuran was treated with 1.74 g of 5-chloroindole at 0° and stirred at this temperature for 1 hour. After the addition of 1.6 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with 11 ml of water. The mixture was diluted with 300 ml of ether, washed with 140 ml of water 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 2.1 g (87%) of (RS)-1-(5-chloro-indol-1-yl)-propan-2-ol as a yellow oil.

Workup

  1. stirringwas stirred at room temperature for 48 hours
  2. washwashed with 140 ml of water and with 70 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 60 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-1aac06e8bb6647b2a634a69046502d62
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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