Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 59442983, compound

HRID 1959116Notes

Reaction equation

HRID 1959116 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=O)=[C:4]([OH:17])[CH:3]=1.C[O:19][C:20](=O)[CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[CH:21][C:20](=[O:19])[O:17]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 25517Ammonium ChlorideHCID 10060688HCID 10060688, compound

Product 1

HCID 59442983HCID 59442983, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under argon atmosphere, a mixture of (4-chloro-2-hydroxyphenyl)(4-fluorophenyl)methanone (1.00 and methyl(triphenylphosphoranylidene)acetate (3.00 g) in toluene (15 mL) was heated under reflux for 15 hours. After cooling, the reaction solution was poured into a saturated aqueous solution of ammonium chloride and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of sodium bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=95/5 to 85/15) and the product was triturated in n-hexane-diisopropyl ether to give the titled compound (0.54 g) as a pale yellow powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with a saturated aqueous solution of sodium bicarbonate and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=95/5 to 85/15)
  9. customthe product was triturated in n-hexane-diisopropyl ether

Sources & evidence

ORD record
ord-8bbc661bdd1c4964adf5932aa49e4ceb
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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