Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 58978089, compound

HRID 1179493Notes

Reaction equation

HRID 1179493 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[NH2:1][C:2]1[CH:9]=[C:8]([F:10])[C:5](/[CH:6]=[CH:17]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 299434504-Amino-2,6-difluorobenzaldehyde

Product 1

HCID 58978089HCID 58978089, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solid mixture of 4-amino-2,6-difluoro-benzaldehyde (6.5 g, 41.4 mmol, 1.0 equiv.) and (carbethoxymethylene)triphenylphosphorane (18.75 g, 53.8 mmol, 1.3 equiv.) at 23° C. was added ethanol (97 mL). After stirring for 25 min at 23° C., the reaction mixture was concentrated, pre-absorbed with silica gel and purified by flash column chromatography eluting with a gradient increasing in polarity from 0 to 30% ethyl acetate in hexane. Relevant fractions were combined to give the desired compound.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompre-absorbed with silica gel
  3. custompurified by flash column chromatography
  4. washeluting with
  5. temperaturea gradient increasing in polarity from 0 to 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-474a2af00cce4052bd2d3929749d229a
Source dataset
uspto-grants-2007_10
Patent number
US07279494B2

Reaction notes

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