2-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one → 2-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one

HRID 465416Notes

Reaction equation

HRID 465416 reaction equation
[CH2:1]([C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][C:11]2[O:12][CH:13]=[C:14]([OH:18])[C:15](=[O:17])[CH:16]=2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=O.C(=O)(O)O.[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]([OH:35])[CH2:33][NH2:34])[CH:29]=[CH:30][CH:31]=1>C1C=CC=CC=1>[Cl:25][C:26]1[CH:27]=[C:28]([CH:29]=[CH:30][CH:31]=1)[CH:32]([OH:35])[CH2:33][NH:34][CH:2]([CH3:4])[CH2:1][C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][C:11]2[O:12][CH:13]=[C:14]([OH:18])[C:15](=[O:17])[CH:16]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 198745552-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-oneHCID 678659382-(3-Chlorophenyl)-2-hydroxyethylamine carbonate

Product 1

HCID 198745272-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-oneYield 10.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one (0.7 g) and 2-(3-chlorophenyl)-2-hydroxyethylamine carbonate 0.52 g in benzene was heated under reflux for 2.5 h using a Dean and Stark head. The reaction mixture was allowed to cool and the solvent removed in vacuo. The residue was taken up in methanol, treated with sodium cyanoborohydride (0.2 g) and stirred at ambient temperature for 18 h. The solvent was evaporated under reduced pressure, the residue dissolved in ethyl acetate, washed with water (2×50 ml), brine(1×50 ml) and dried (magnesium sulphate). After filtration and evaporation of solvent the residue was purified by column chromatography on silica using methanol:chloroform (3:97) as eluent, followed by crystallisation from acetone to give 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one, (0.1 g), as a (35:65) mixture of diastereoisomers.

Workup

  1. temperatureunder reflux for 2.5 h
  2. temperatureto cool
  3. customthe solvent removed in vacuo
  4. additiontreated with sodium cyanoborohydride (0.2 g)
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionthe residue dissolved in ethyl acetate
  7. washwashed with water (2×50 ml), brine(1×50 ml)
  8. dry with materialdried (magnesium sulphate)
  9. filtrationAfter filtration and evaporation of solvent the residue
  10. customwas purified by column chromatography on silica
  11. customfollowed by crystallisation from acetone

Sources & evidence

ORD record
ord-1df474a9044944edaf069ecfc3e51a7e
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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