Potassium Carbonate → HCID 59472624, compound

HRID 885142Notes

Reaction equation

HRID 885142 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].C[C:13]1[N:14]=[CH:15][NH:16][CH:17]=1.[C:18]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CN(C=O)C.CCOC(C)=O.C(Cl)Cl>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:14]2[CH:13]=[CH:17][N:16]=[CH:15]2)=[C:3]([O:10][CH3:11])[CH:4]=1)#[CH:18]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27373584-Fluoro-3-methoxybenzaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-oneHCID 178418800HCID 178418800, compound

Product 1

HCID 59472624HCID 59472624, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-fluoro-3-methoxybenzaldehyde (1.0 g, 6.5 mmol) in 20 mL of DMF was treated with 4-methylimidazole (1.0 g, 15 mmol) and warmed to 130° C. Stirred overnight. Diluted with EtOAc, washed with sat'd NaHCO3, dried (Na2SO4), concentrated. Dissolved in 20 mL of MeOH, treated with K2CO3 (2.0 g, 14 mmol) and dimethyl (1-diazo-2-oxopropyl)phosphonate (1.5 g, 7.8 mmol) and stirred overnight. Diluted with DCM and washed with water. Dried (Na2SO4), conc. Chromatography on silica (0-20% MeOH/DCM) gave the desired alkyne:

Workup

  1. washwashed with sat'd NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. dissolutionDissolved in 20 mL of MeOH
  5. stirringstirred overnight
  6. washwashed with water
  7. dry with materialDried (Na2SO4), conc. Chromatography on silica (0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-d577c926964246b994ac1d5beee3815e
Source dataset
uspto-grants-2012_08
Patent number
US08242150B2

Reaction notes

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