Potassium Carbonate → HCID 118659408, compound

HRID 1477237Notes

Reaction equation

HRID 1477237 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([O:17][CH2:18]C)=[O:16])[CH:10]=2)=[CH:5][CH:4]=1)=O.[CH3:20]/C(/[O-])=C(/P(OC)(OC)=O)\[N+]#N.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:10]=2)=[CH:7][CH:8]=1)#[CH:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 90012314HCID 90012314, compoundHCID 178502985HCID 178502985, compound

Product 1

HCID 118659408HCID 118659408, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirring solution of compound 2.5 (12.7 g, 50 mmol) in CH3OH (300 mL) was added the Bestmann reagent (14.4 g, 75 mmol) followed by K2CO3 (20.8 g, 150 mmol) and the reaction was stirred for 5 hr. The reaction mixture was diluted with water (500 mL) and extracted with Et2O (3×300 mL). The combined organic layers were dried and concentrated under reduced pressure to give a crude, which was purified by flash chromatography (silica gel/PE:Et2O 10:1-5:1) to give methyl 4-(4-ethynylphenyl)picolinate (2.6, 4.0 g, 33.9%) as a white solid.

Workup

  1. extractionextracted with Et2O (3×300 mL)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude, which
  5. customwas purified by flash chromatography (silica gel/PE:Et2O 10:1-5:1)

Sources & evidence

ORD record
ord-cc49a690561a45c58afc9fa13ad20cf4
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

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