Potassium Carbonate → HCID 86601217, compound

HRID 349264Notes

Reaction equation

HRID 349264 reaction equation
[CH3:1]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.[F:13][C:14]([F:40])([F:39])[C:15]1[CH:16]=[C:17]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:18][N:19]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:22]([CH:30]=O)[N:21]=[N:20]1.C(=O)([O-])[O-].[K+].[K+]>CO.CCOCC.C([O-])(O)=O.[Na+]>[F:13][C:14]([F:40])([F:39])[C:15]1[CH:16]=[C:17]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:18][N:19]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:22]([C:30]#[CH:1])[N:21]=[N:20]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 86601210HCID 86601210, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86601217HCID 86601217, compoundYield 53.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To the (1-Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (794 mg, 4.20 mmol) in 70 mL of methanol, add 1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazole-4-carbaldehyde (1.44 g, 3.60 mmol) as a solution in 5 mL of methanol. To this mix, add (995 mg, 7.20 mmol) of potassium carbonate and mix the solution for 18 h. Dilute with ether and saturated NaHCO3, and extract with ether 3 times, wash the organics again with saturated NaHCO3, and dry the combined organics with MgSO4. Filter and concentrate. Purify by chromatography (silica gel, hexanes/EtOAc gradient) to provide 764 mg of the title compound. Exact Mass 395.09 spectrum (aspci): m/z=396.1 (M+1), 394.0 (M−1); 1H NMR (250 MHz, CDCl3) δ 7.73 (s, 1H), 7.55–7.40 (m, 4H), 7.42–7.30 (m, 3H), 5.52 (s, 2H), 3.21 (s, H).

Workup

  1. additionmix the solution for 18 h
  2. extractionextract with ether 3 times
  3. washwash the organics again with saturated NaHCO3
  4. dry with materialdry the combined organics with MgSO4
  5. filtrationFilter
  6. concentrationconcentrate
  7. customPurify by chromatography (silica gel, hexanes/EtOAc gradient)

Sources & evidence

ORD record
ord-441e8da3a164405998d9d6fd93e86dd1
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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