Potassium Carbonate → 2-Ethynyl-5-isopropoxypyridine

HRID 76124

Reaction equation

HRID 76124 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]=O)=[N:9][CH:10]=1)([CH3:3])[CH3:2].[C:13]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO.CCOC(C)=O>[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:10][N:9]=1)#[CH:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 797940465-IsopropoxypicolinaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 747887042-Ethynyl-5-isopropoxypyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1.00 g (6.05 mmol) 5-isopropoxypicolinaldehyde in 20 mL methanol are added 1.67 g (12.1 mmol) K2CO3 followed by 1.4 g (7.26 mmol) dimethyl 1-diazo-2-oxopropylphosphonate. After stirring at r.t. over the weekend the reaction mixture is diluted with EtOAc and washed consecutively with NaHCO3 solution and water. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo.

Workup

  1. washwashed consecutively with NaHCO3 solution and water
  2. dry with materialThe organic layer is dried with Na2SO4
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-a170e6da9b254ca38b9dff72e944b64c
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Linked notes

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