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Triethylamine → 1-(4-Methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dione

HRID 351539
Notes
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Reaction equation

HRID 351539 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH:15]=[CH2:16])=[O:14])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=[O:18].C(N(CC)CC)C>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[CH3:26][O:25][C:23]([C:22]1[CH:27]=[CH:28][C:19]([C:17](=[O:18])[CH2:16][CH2:15][C:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:12][CH:11]=2)=[O:14])=[CH:20][CH:21]=1)=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15294Methyl 4-FormylbenzoateHCID 227132221-(4-n-Pentyloxyphenyl)acrolein

Product 1

HCID 227132231-(4-Methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dioneYield 81.8%

Reagents, catalysts & solvents 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride
Catalyst
HCID 702EthanolSolvent

Procedure

A suspension of 1-(4-n-pentyloxyphenyl)acrolein (2.38 g), methyl 4-formylbenzoate (1.97 g), 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride and triethylamine (0.91 ml) in ethanol (10 ml) was refluxed for 18 hours. After cooling, the solvents were removed under reduced pressure. The solids were taken up in 1N HCl and extracted with dichloromethane. The organic layer was washed successively with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, collected by filtration and dried under reduced pressure to give 1-(4-methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dione (3.41 g).

Workup

  1. temperaturewas refluxed for 18 hours
  2. temperatureAfter cooling
  3. customthe solvents were removed under reduced pressure
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed successively with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with diisopropyl ether
  9. filtrationcollected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-1dfc266d3ef0430ca5d5774187bb1e33
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06743776B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes