Potassium Carbonate → HCID 59472598, compound

HRID 885141Notes

Reaction equation

HRID 885141 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1.[C:23]([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:21]2[CH:22]=[C:18]([CH3:17])[N:19]=[CH:20]2)=[C:3]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=1)#[CH:23]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-oneHCID 178418800HCID 178418800, compound

Product 1

HCID 59472598HCID 59472598, compoundYield 87.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluoro-3-phenoxybenzaldehyde (1.0 g, 4.6 mmol) in 10 mL of DMF was treated with 4-methylimidazole (1.0 g, 12 mmol) and warmed to 100° C. Stirred overnight. Diluted with EtOAc, washed with sat'd NaHCO3, dried (Na2SO4), concentrated. Dissolved in 10 mL of MeOH, treated with K2CO3 (1.0 g, 7.2 mmol) and dimethyl (1-diazo-2-oxopropyl)phosphonate (1.0 g, 5.2 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 (1.1 g; 87% overall yield):

Workup

  1. washwashed with sat'd NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. dissolutionDissolved in 10 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-8f13918b336944ff92123d4033d6249d
Source dataset
uspto-grants-2012_08
Patent number
US08242150B2

Reaction notes

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