Potassium Carbonate → HCID 15079657, compound

HRID 476511Notes

Reaction equation

HRID 476511 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:6][C:5]([N:16]2[C:20](=[O:21])[N:19]([CH2:22][CH2:23][CH2:24][F:25])[N:18]=[N:17]2)=[C:4]([F:26])[CH:3]=1.Br[CH:28]([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([F:26])[C:5]([N:16]2[C:20](=[O:21])[N:19]([CH2:22][CH2:23][CH2:24][F:25])[N:18]=[N:17]2)=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:28]([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 15079652HCID 15079652, compound

Product 1

HCID 15079657HCID 15079657, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 1.0 g (0.0026 mole) of 1-[4-chloro-2-fluoro-5-(4-hydroxyphenoxy)phenyl]-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one, 1.5 g (0.0083 mole) of ethyl 2-bromopropionate, and 0.64 g (0.0046 mole) of potassium carbonate in 50 ml of acetone was heated at reflux for approximately 18 hours. The mixture was cooled and the solvent was removed by evaporation under reduced pressure leaving a residue. This residue was purified by column chromatography on silica gel, eluting with methylene chloride to yield 0.5 g of ethyl 2-[4-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-1,4-dihydro-5-oxotetrazol-1-yl]phenoxy]phenoxy]propionate as an oil, compound 8 of Table 1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 18 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed by evaporation under reduced pressure
  5. customleaving a residue
  6. customThis residue was purified by column chromatography on silica gel
  7. washeluting with methylene chloride

Sources & evidence

ORD record
ord-4b80bcb6d30b4b2a8c6976a8fba1095b
Source dataset
uspto-grants-1989_12
Patent number
US04885025

Reaction notes

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