Epichlorohydrin → 1-Oxiranylmethylindole-5-carbonitrile

HRID 1821956Notes

Reaction equation

HRID 1821956 reaction equation
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[O:18]1[CH2:17][CH:16]1[CH2:14][N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 27513Indole-5-carbonitrile

Product 1

HCID 468686361-Oxiranylmethylindole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.07 g (42 mmol) pulverized, 88% potassium hydroxide, 3.0 g (0.021 mol) indole-5-carbonitrile and 0.68 g (2 mmol) tetrabutylammoniumbromide are jointly weighed out in the given order and mixed with 9.9 ml (126 mmol) epichlorohydrine with stirring. Stirring is continued overnight. Following hydrolysis and three extractions using ethyl acetate, the combined organic phases are washed three times with water. Drying of the organic phase using sodium sulfate and concentration of the solvent on the rotary evaporator leaves a solid which is purified on silica gel by column chromatography (flow agent: hexane/ethyl acetate 7:3).

Workup

  1. stirringStirring
  2. customhydrolysis and three extractions
  3. washthe combined organic phases are washed three times with water
  4. customDrying of the organic phase
  5. customon the rotary evaporator
  6. customleaves a solid which
  7. customis purified on silica gel by column chromatography (flow agent: hexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-7f079bb7f23148359c3fd485250c23b6
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

Loading…