Tosylmethyl isocyanide → HCID 68682374, compound

HRID 2263616Notes

Reaction equation

HRID 2263616 reaction equation
CC(C)([O-])C.[K+].CC1C=CC(S([CH2:17][N+:18]#[C-])(=O)=O)=CC=1.[CH:20]1([CH2:23][S:24][CH:25]2[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]2)[CH2:22][CH2:21]1>COCCOC.C(OCC)(=O)C>[CH:20]1([CH2:23][S:24][CH:25]2[CH2:30][CH2:29][CH:28]([C:17]#[N:18])[CH2:27][CH2:26]2)[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 68683678HCID 68683678, compound

Product 1

HCID 68682374HCID 68682374, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium-t-butoxide (16.10 g, 144 mmol) was added to a stirred, cooled (0° C.) mixture of TOSMIC (15.84 g, 81 mmol) and 4-[(cyclopropylmethyl)thio]cyclohexanone (11.5 g, 62.4 mmol) in DME (125 ml) and the mixture was stirred at room temperature for 3 h. The mixture was cooled, diluted with ethyl acetate, washed with brine, dried, filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a Biotage 65i cartridge, eluting with EtOAc/isohexane to give two separated isomers. Combined yield of 4-[(cyclopropylmethyl)thio]cyclohexanecarbonitrile (7.1 g, 36.3 mmol, 58.3% yield)

Workup

  1. temperaturecooled
  2. temperatureThe mixture was cooled
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using a Biotage 65i cartridge
  8. washeluting with EtOAc/isohexane
  9. customto give two separated isomers

Sources & evidence

ORD record
ord-fc000f4e2eac457ba2049efc5986274d
Source dataset
uspto-grants-2010_12
Patent number
US07851638B2

Reaction notes

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