Tosylmethyl isocyanide → HCID 11816413, compound

HRID 1989819Notes

Reaction equation

HRID 1989819 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=O)[CH3:11].S([CH2:23][N+:24]#[C-])(C1C=CC(C)=CC=1)(=O)=O.CC([O-])(C)C.[K+]>COCCOC.CC(O)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:11])[C:23]#[N:24]

Participants

6

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 112524022'-CHLORO-4'-HYDROXYACETOPHENONEHCID 23665647Potassium tert-butoxide

Product 1

HCID 11816413HCID 11816413, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2′-chloro-4′-methoxyacetophenone (18.5 g, 0.10 mol) and tosylmethylisocyanide (TOSMIC, 21.5 g, 0.11 mol) in dry 1,2-dimethoxyethane (100 mL) was cooled to −10° C. A solution of t-BuOK (22.4 g, 0.20 mol) in dry t-BuOH (250 mL) was added slowly keeping the temperature below 5° C. The homogeneous orange solution was stirred for 2 h/0° C. and 1 h/25° C. The resulting suspension was evaporated to a slurry. Water (200 mL) was added and extracted with Et2O (3×150 mL). The organic phase was dried (Na2SO4) and the solvent was removed under reduced pressure leaving an orange oil. Yield: 19 g (97%). GCMS: >98%

Workup

  1. customthe temperature below 5° C
  2. customThe resulting suspension was evaporated to a slurry
  3. additionWater (200 mL) was added
  4. extractionextracted with Et2O (3×150 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customthe solvent was removed under reduced pressure
  7. customleaving an orange oil

Sources & evidence

ORD record
ord-19229dc1a7fb402288e9897e758debe6
Source dataset
uspto-grants-2010_01
Patent number
US07642367B2

Reaction notes

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