Acetone → HCID 13745626, compound

HRID 986696Notes

Reaction equation

HRID 986696 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[F:22])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2].CC(C)=O.[CH3:33][N:34]([CH3:39])[CH2:35][CH2:36][CH2:37]O.C(N(CC)CC)C>C(Cl)(Cl)Cl.S(Cl)(Cl)=O>[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([O:19][CH2:37][CH2:36][CH2:35][N:34]([CH3:39])[CH3:33])=[O:18])=[CH:15][C:14]=2[F:22])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 766463-(Dimethylamino)-1-propanolHCID 13745623HCID 13745623, compound

Product 1

HCID 13745626HCID 13745626, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-fluorobenzoic acid (220 mg) in chloroform (2 ml) and thionyl chloride (0.4 ml) was refluxed for 20 minutes, then the solvent was removed under reduced pressure. To the residue was added toluene, and then the solvent was removed under reduced pressure. To the residue thus obtained was added acetone (5 ml), 3-dimethylaminopropanol (70 mg) and triethylamine (0.25 ml), and the mixture was refluxed for 0.5 hour. The precipitated colorless crystals were removed by filtration, and the filtrate was concentrated. The residue was dissolved in chloroform, and the solution was washed once with a saturated sodium hydrogen carbonate, and dried with sodium sulfate. The solvent was removed by evaporation and to the cooled residue was added hexane to give colorless crystals of 3-dimethylaminopropyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-fluorobenzoate (140 mg). m.p. 55°-56° C.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionTo the residue was added toluene
  3. customthe solvent was removed under reduced pressure
  4. customTo the residue thus obtained
  5. temperaturethe mixture was refluxed for 0.5 hour
  6. customThe precipitated colorless crystals were removed by filtration
  7. concentrationthe filtrate was concentrated
  8. dissolutionThe residue was dissolved in chloroform
  9. washthe solution was washed once with a saturated sodium hydrogen carbonate
  10. dry with materialdried with sodium sulfate
  11. customThe solvent was removed by evaporation and to the cooled residue
  12. additionwas added hexane

Sources & evidence

ORD record
ord-1070c1aea2cd4d8dbcc8e041c10582ef
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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