Water → HCID 10848515, compound

HRID 2396838Notes

Reaction equation

HRID 2396838 reaction equation
[H-].[Na+].[Br: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>[Br: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 249055-Bromoindole

Product 1

HCID 10848515HCID 10848515, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.56 g of sodium hydride dispersion in 75 ml of tetrahydrofuran was treated with 2.95 g of 5-bromoindole at 0° C. and stirred at this temperature for 1 hour. After the addition of 2.1 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 60 hours and subsequently treated with 15 ml of water. The mixture was diluted with 750 ml of ether, washed twice with 250 ml of water and with 125 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 120 g of silica gel with toluene-ethyl acetate (19:1). There were obtained 3.4 g (89%) of (RS)-1-(5-bromo-indol-1-yl)-propan-2-ol as a yellow oil.

Workup

  1. stirringwas stirred at room temperature for 60 hours
  2. washwashed twice with 250 ml of water and with 125 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 120 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-bd83cc7297f5431dbdd9f638116f1a41
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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