Hydrochloric Acid → 153580-00-8

HRID 1168618Notes

Reaction equation

HRID 1168618 reaction equation
S([CH2:11][N+:12]#[C-])(C1C=CC(C)=CC=1)(=O)=O.CC(C)([O-])C.[K+].[CH3:20][C:21]1([CH3:27])[CH2:25][CH2:24][CH2:23][C:22]1=O.Cl>CS(C)=O.CO.C(OCC)(=O)C>[CH3:20][C:21]1([CH3:27])[CH2:25][CH2:24][CH2:23][CH:22]1[C:11]#[N:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1382862,2-DimethylcyclopentanoneHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

Product 1

HCID 10057496153580-00-8Yield 31%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Tosylmethyl isocyanide (3.76 g, 19.3 mmol) was dissolved in dimethylsulfoxide (15 mL) and cooled to 0° C. Solid potassium t-butoxide (6.3 g, 59.2 mmol) was added and a thick brown precipitate formed. The reaction mixture was warmed to room temperature and 2,2-dimethylcyclopentanone (2.0 mL, 16.0 mmol) was added in anhydrous methanol (680 μL) and the reaction mixture was stirred for 30 hours. It was diluted with ethyl acetate, acidified with hydrochloric acid and extracted with hexanes. The extracts were dried over magnesium sulfate, filtered and the solvent was removed to provide a brown oil which was purified by chromatography on silica gel eluted with 0-50% dichloromethane in hexanes to yield a yellow oil (612 mg, 31%).

Workup

  1. customa thick brown precipitate formed
  2. temperatureThe reaction mixture was warmed to room temperature
  3. extractionextracted with hexanes
  4. dry with materialThe extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed
  7. customto provide a brown oil which
  8. customwas purified by chromatography on silica gel
  9. washeluted with 0-50% dichloromethane in hexanes

Sources & evidence

ORD record
ord-19a1f69ddc1c462ea97473e6666a72ac
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

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