Triethylamine → ETHYL 3-(4-FORMYLPHENYL)PROPANOATE

HRID 555498

Reaction equation

HRID 555498 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][CH:13]([O:16]CC)[CH:14]=[CH2:15])[CH3:11].C(N(CC)CC)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:10]([O:12][C:13](=[O:16])[CH2:14][CH2:15][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH3:11]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 624773,3-Diethoxy-1-propeneHCID 966574-Iodobenzaldehyde

Product 1

HCID 12169276ETHYL 3-(4-FORMYLPHENYL)PROPANOATEYield 711.8%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-iodobenzaldehyde (0.116 g, 0.5 mmol), acrolein diethylacetal (0.3 mL, 1.5 mmol), tetra-n-butylammonium chloride (0.139 g, 0.5 mmol) and triethylamine in anhydrous dimethylformamide (2 mL), palladium acetate (0.003 g, 0.015 mmol) was added. The reaction mixture was heated at 90° C. and stirred for 16 h. The reaction mixture was diluted with 2 N hydrochloric acid and extracted with diethyl ether. The solvent was evaporated in vacuo to leave a residue which was purified by column chromatography (silica gel) employing 1-5% ethyl acetate in hexane as eluents to obtain 3-(4-formyl-phenyl)-propionic acid ethyl ester (0.734 g).

Workup

  1. extractionextracted with diethyl ether
  2. customThe solvent was evaporated in vacuo
  3. customto leave a residue which
  4. customwas purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-c5cf0138ff694247a457dc8ccc94abf0
Source dataset
uspto-grants-2011_11
Patent number
US08053440B2

Linked notes

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