Triethylamine → HCID 54343021, compound

HRID 1872397

Reaction equation

HRID 1872397 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:15]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH2:18][CH3:19].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.[Ti](Cl)(Cl)(Cl)Cl>[CH2:15]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[CH:2][C:1]([C:4]2[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=2)=[O:3])=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 79815p-PentoxybenzaldehydeHCID 600911Ethyl 4-acetylbenzoate

Product 1

HCID 54343021HCID 54343021, compoundYield 61.2%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of titanium(IV) chloride (13.88 g) in dichloromethane (100 ml) was added Ethyl 4-acetylbenzoate (11.53 g) and 4-n-pentyloxybenzaldehyde (12.68 g) in dichloromethane (50 ml) was added dropwise at 0° C. To the mixture was added triethylamine (12.44 ml) in dichloromethane (30 ml). The mixture was stirred at 0° C. for 30 minutes and diluted with ethyl acetate. The organic layer was washed with water (four times) and brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with n-hexane. The solid was collected by filtration and dried to give 1-(4-n-Pentyloxyphenyl)-3-(4-ethoxycarbonylphenyl)-1-propen-3-one (13.45 g).

Workup

  1. additionwas added dropwise at 0° C
  2. washThe organic layer was washed with water (four times) and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvents were removed under reduced pressure
  5. customthe residue was triturated with n-hexane
  6. filtrationThe solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-5929b187f2df40f981646c2892dd1128
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Linked notes

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