Sodium Bicarbonate → 2-(2-Ethynylphenyl)propanamide

HRID 592355Notes

Reaction equation

HRID 592355 reaction equation
C([Si]([C:8]#[C:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([CH3:20])[C:17]([NH2:19])=[O:18])(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([CH3:20])[C:17]([NH2:19])=[O:18])#[CH:8]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 867122782-(2-((Triethylsilyl)ethynyl)phenyl)propanamide

Product 1

HCID 867122792-(2-Ethynylphenyl)propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled (0° C. water/ice bath) solution of 2-(2-((triethylsilyl)ethynyl)phenyl)propanamide I14 (7.17 g, 24.9 mmol) in THF (40 mL) was slowly treated with a 1.0 M solution of tetrabutylammonium fluoride in THF (26.2 mL, 26.2 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at 0° C. for 5 minutes before a sat. aq. NaHCO3 solution was added. The mixture was extracted with EtOAc (3 times), the combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo to give the crude product. The crude product was purified by silica gel column chromatography (Combiflash Rf, 30-80% EtOAc in cyclohexane) to give the title compound K7 as a cream solid (3.69 g, 85%). LCMS-B: rt 3.031 min; m/z 174 [M+H]+.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc (3 times)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customto give the crude product
  7. customThe crude product was purified by silica gel column chromatography (Combiflash Rf, 30-80% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-deb63e7d9e0c482e8af97b55433afe6f
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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