Methyl Acrylate → HCID 10800655, compound

HRID 1016742Notes

Reaction equation

HRID 1016742 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:37]1[C:42]([CH:43]=[O:44])=[CH:41][C:40]([O:45][CH3:46])=[C:39]([O:47][CH3:48])[CH:38]=1>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].O.C(OCC)(=O)C>[CH:43]([C:42]1[CH:41]=[C:40]([O:45][CH3:46])[C:39]([O:47][CH3:48])=[CH:38][C:37]=1/[CH:3]=[CH:2]/[C:1]([O:5][CH3:6])=[O:4])=[O:44]

Participants

9

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 793516-Bromo-3,4-dimethoxybenzaldehydeHCID 80271Tri-o-tolylphosphine

Product 1

HCID 10800655HCID 10800655, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

6.2 ml of methyl acrylate, 25 ml of triethylamine, 270 mg of Pd(OAc)2 and 1.5 g of tri-(o-tolyl)-phosphine were added to a solution of 14.7 g of 6-bromoveratraldehyde in 100 ml of dimethylacetamide. The reaction mixture was heated for 4 hours to 110° C., then left to cool to room temperature and poured into a mixture of ethyl acetate and water. The crude product was extracted and purified by chromatography on silica gel and yielded 10.8 g of methyl (E)-3-(2-formyl-4,5-dimethoxy-phenyl)-acrylate as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated for 4 hours to 110° C.
  2. waitleft
  3. extractionThe crude product was extracted
  4. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-7e5498c4f60346e9aec9d19e38abdfb8
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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