Water → HCID 10702816, compound

HRID 2396839Notes

Reaction equation

HRID 2396839 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.[CH3:13][CH:14]1[CH2:16][O:15]1.O>O1CCCC1.CCOCC>[CH3:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][CH:14]([OH:15])[CH3:16])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6378Propylene OxideHCID 24758Sodium hydrideHCID 1379281H-Indole, 6-methyl-

Product 1

HCID 10702816HCID 10702816, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.28 g of sodium hydride dispersion in 40 ml of tetrahydrofuran was treated with 0.98 g of 6-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 60 hours and subsequently treated with 7 ml of water. The mixture was diluted with 370 ml of ether, washed twice with 120 ml of water and with 60 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 35 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.5 g (35%) of (RS)-1-(6-methyl-indol-1-yl)-propan-2-ol as light brown crystals with m.p. 65°-69°.

Workup

  1. stirringwas stirred at room temperature for 60 hours
  2. washwashed twice with 120 ml of water and with 60 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 35 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-0c5636f28a9d45daa7fd561deb72b7d1
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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