Water → HCID 67305706, compound

HRID 876814Notes

Reaction equation

HRID 876814 reaction equation
[N+](C1C=C([N+]([O-])=O)C=CC=1[O-])([O-])=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:17][CH:16]=1.[C:30]([O:34][CH3:35])(=[O:33])[C:31]#[CH:32].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Si:23]([O:22][CH2:21][C:18]1[CH:19]=[CH:20][N:15]2[N:14]=[CH:32][C:31]([C:30]([O:34][CH3:35])=[O:33])=[C:16]2[CH:17]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13536Methyl propiolateHCID 86671435HCID 86671435, compound

Product 1

HCID 67305706HCID 67305706, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-amino-4-((tert-butyldimethylsilyloxy)methyl)pyridinium 2,4-dinitrophenolate Y-4 (13.4 g, 31.6 mmol) in DMF (60 mL) were added methyl propiolate (2.7 g, 31.6 mmol) and K2CO3 (6.5 g, 47.4 mmol). The reaction was stirred at room temperature for 24 h, then treated with water. The resulting mixture was extracted with ethyl acetate (100 ml×3), the combined organic layers were washed with water, brine and dried over Na2SO4, then concentrated in vacuo, the residue was purified by silica gel chromatography to afford the title compound (2.9 g). MS (m/z): 321 (M+1)+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (100 ml×3)
  2. washthe combined organic layers were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5570bc3ad97547ab89fe31e0b005c947
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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