HCID 59384258, compound → HCID 11645398, compound

HRID 2356605Notes

Reaction equation

HRID 2356605 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]([CH3:24])=[CH2:23])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17]CC)=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]([CH3:24])=[CH2:23])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 59384258HCID 59384258, compound

Product 1

HCID 11645398HCID 11645398, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 6-({5-chloro-2-[(2-methyl-2-propen-1-yl)oxy]phenyl}methyl)-2-pyridinecarboxylate (60 mg, 0.17 mmol) was stirred at 60° C. for 2 hours in ethanol (3 ml) and 2M sodium hydroxide solution (0.4 ml). The reaction mixture was cooled and evaporated. The residue was diluted with water and extracted with diethyl ether. The aqueous phase was then acidified with glacial acetic acid and extracted with ethyl acetate (2×20 ml), dried (MgSO4) and evaporated to give the title compound as a yellow oil (38 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated
  3. additionThe residue was diluted with water
  4. extractionextracted with diethyl ether
  5. extractionextracted with ethyl acetate (2×20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-75404dd725784b999819752428deab86
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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