Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 86621313, compound

HRID 238303Notes

Reaction equation

HRID 238303 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][CH:3]=1.[CH3:10][O:11][C:12](=[O:33])[CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[CH3:10][O:11][C:12](=[O:33])/[CH:13]=[CH:8]/[C:5]1[CH:6]=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 86621313HCID 86621313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.045 g (27.12 mmol) of 6-bromopyridine-3-carbaldehyde were dissolved in 50 ml of THF. 9.068 g (27.12 mmol) of 2-(triphenylphosphoranylidene)acetic acid methyl ester were added and the mixture was stirred at RT for 4 hours. After evaporation, the residue stirred with methanol and the solid was filtered off. The filtrate was evaporated and the residue was purified by chromatography (silica gel, ethyl acetate/n-heptane 1:4). Yield: 5.01 g (76.3%)

Workup

  1. customAfter evaporation
  2. stirringthe residue stirred with methanol
  3. filtrationthe solid was filtered off
  4. customThe filtrate was evaporated
  5. customthe residue was purified by chromatography (silica gel, ethyl acetate/n-heptane 1:4)

Sources & evidence

ORD record
ord-48461e30dac0473fa0126ab69d09bf50
Source dataset
uspto-grants-2014_02
Patent number
US08642620B2

Reaction notes

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