Phenol → HCID 58885445, compound

HRID 1766281Notes

Reaction equation

HRID 1766281 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4](Cl)[C:5](=[O:8])[CH2:6][CH3:7].C1(O)C=CC=CC=1.[C:18]([C:20]1[CH:21]=[C:22]([OH:28])[CH:23]=[C:24]([C:26]#[N:27])[CH:25]=1)#[N:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O.O>[CH3:1][O:2][C:3](=[O:10])[CH:4]([O:28][C:22]1[CH:21]=[C:20]([C:18]#[N:19])[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=1)[C:5](=[O:8])[CH2:6][CH3:7]

Participants

7

Reactant 4

HCID 996PhenolHCID 10796Cesium carbonateHCID 545096Methyl 2-chloro-3-oxopentanoateHCID 219498745-Hydroxybenzene-1,3-dicarbonitrile

Product 1

HCID 58885445HCID 58885445, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A solution of 2-chloro-3-oxo-pentanoic acid methyl ester (20 g, 121.5 mmol) in acetone (100 ml) was added to the phenol from Preparation 3 (17.5 g, 121.5 mmol) and caesium carbonate (43.5 g, 133.6 mmol) in acetone (400 ml) under a nitrogen atmosphere. The mixture was stirred at room temperature for 15 minutes and then heated under reflux for 2.5 hours. Water was added and the solvent was evaporated under reduced pressure. The residual aqueous solution was extracted with dichloromethane (3×300 ml) and the combined organic layers were dried over magnesium sulphate and evaporated under reduced pressure. The residual orange oil was pre-adsorbed onto silica gel and then purified by chromatography on silica gel using ethyl acetate in pentane (gradient from 20:80 to 80:20) to give the title compound as a yellow solid (27 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5 hours
  3. customthe solvent was evaporated under reduced pressure
  4. extractionThe residual aqueous solution was extracted with dichloromethane (3×300 ml)
  5. dry with materialthe combined organic layers were dried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-fae893c92cdd487eb474f62914e13034
Source dataset
uspto-grants-2007_06
Patent number
US07230025B2

Reaction notes

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