Potassium Carbonate → HCID 59745015, compound

HRID 2402428Notes

Reaction equation

HRID 2402428 reaction equation
[CH3:1]OP(CC(=O)C)(=O)OC.C([O-])([O-])=O.[K+].[K+].O=[CH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=1>CC#N.CO>[CH2:20]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=1)[CH2:19][C:18]#[CH:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 54208139HCID 54208139, compound

Product 1

HCID 59745015HCID 59745015, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Dimethyl-2-oxopropylphosphonate (1.2 equiv, 1.5 g, 9.1 mmol) was added to a suspension of K2CO3 (3 equiv, 3.1 g, 23 mmol) and p-TsN3 (1.2 equiv, 1.8 g, 9.1 mmol) in MeCN (144 mL). The mixture was then stirred for 2 h. A solution of the methyl 2-(4-(3-oxopropyl)phenyl)acetate (1 equiv, 1.56 g, 7.6 mmol) in MeOH was then added in one portion and the reaction was stirred overnight. The solvent was evaporated under reduced pressure. The residue was partitioned between Et2O (100 mL) and water (100 mL). The aqueous phase was separated and extracted with Et2O (25 mL) twice. The organic phases were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash column eluting with 0-30% EtOAc in hexanes to afford methyl 2-(4-(but-3-ynyl)phenyl)acetate in 980 mg (64%). LRMS: 202.5 (calc) 225.1 (found)(MNa)+.

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customThe residue was partitioned between Et2O (100 mL) and water (100 mL)
  4. customThe aqueous phase was separated
  5. extractionextracted with Et2O (25 mL) twice
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel flash column
  10. washeluting with 0-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-fdfa684d41b144eabaf2401aebf27f3c
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

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