Potassium Hydroxide → N-(2-ethynylphenyl)acetamide

HRID 1616616Notes

Reaction equation

HRID 1616616 reaction equation
[OH-].[K+].C[Si](C)(C)[C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:16])[CH3:15]>O.CO>[C:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:16])[CH3:15])#[CH:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 13718035N-(2-trimethylsilanylethynyl-phenyl)-acetamide

Product 1

HCID 10261360N-(2-ethynylphenyl)acetamideYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Add a solution of potassium hydroxide (1.62 g, 28.8 mmol) in water (100 mL) dropwise to a rapidly stirred solution of N-(2-trimethylsilanylethynyl-phenyl)-acetamide (4.44 g, 19.2 mmol) in methanol (50 mL) and stir at room temperature for 4 hours. Concentrate, add brine to residue and extract with EtOAc (×3). Dry combined organic layers over MgSO4, concentrate, add CHCl3 and concentrate to get 2.82 g light yellow solid. Purify the residue by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes to afford the title compound (2.56 g, 84%). MS (IS) 160 (M+1)+.

Workup

  1. concentrationConcentrate
  2. additionadd brine to residue
  3. extractionextract with EtOAc (×3)
  4. customDry
  5. concentrationconcentrate
  6. additionadd CHCl3
  7. concentrationconcentrate
  8. customto get 2.82 g light yellow solid
  9. customPurify the residue by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-5f5bbdedbbe24e3fbdf6976c7a4b18cf
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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