Potassium tert-butoxide → HCID 59762380, compound

HRID 40119Notes

Reaction equation

HRID 40119 reaction equation
[CH3:1][CH:2]([CH3:20])[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[NH:14]C(=O)CCC.CC([O-])(C)C.[K+]>CN1C(=O)CCC1.CCOC(C)=O>[CH:2]([C:3]1[NH:14][C:6]2[C:5]([CH:4]=1)=[CH:10][CH:9]=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=2)([CH3:20])[CH3:1]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59762443N-(2-(3-Methylbut-1-ynyl)-5-nitrophenyl)butyramide2×

Product 1

HCID 59762380HCID 59762380, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-(2-(3-methylbut-1-ynyl)-5-nitrophenyl)butyramide (Compound 119, 900 mg, 3.29 mmol) in NMP (10 ml) was added KOt-Bu (552 mg, 4.94 mmol) and the mixture was stirred at 70° C. for 16 h, cooled to room temperature, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes) to yield the title compound.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes)

Sources & evidence

ORD record
ord-9930116e41c24842af7e9236d560efb7
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

Loading…