Potassium Carbonate → HCID 58608139, compound

HRID 2243576Notes

Reaction equation

HRID 2243576 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[CH:27]=[CH:26][C:16]([O:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:15][CH:14]=1)(C)C>CO>[C:12]([C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)=[CH:26][CH:27]=1)#[CH:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58608154HCID 58608154, compound

Product 1

HCID 58608139HCID 58608139, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (4.15 g, 30.0 mmol) was added to a solution of the 4-[2-(4-trimethylsilanylethynyl-phenoxy)-ethyl]-morpholine 101b in methanol (25 mL). The mixture stirred at room temperature for 2.5 h and was then filtered through a pad of Celite along with dichloromethane. The filtrate was concentrated and partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford an orange oil. This oil was purified via column chromatography (eluting with 50-100% ethyl acetate-hexane) to afford 4-[2-(4-ethynyl-phenoxy)-ethyl]-morpholine 102b as an orange solid. MS (MH+) 232.2; Calculated 231 for C14H17NO2.

Workup

  1. filtrationwas then filtered through a pad of Celite along with dichloromethane
  2. concentrationThe filtrate was concentrated
  3. custompartitioned between dichloromethane and water
  4. customThe aqueous phase was separated
  5. extractionextracted with dichloromethane
  6. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford an orange oil
  11. customThis oil was purified via column chromatography (eluting with 50-100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-6caca30df7c2412a846b5120258ec852
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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