Methyl Acrylate → Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

HRID 1898760Notes

Reaction equation

HRID 1898760 reaction equation
[C:1]([O:4][C:5]1[CH:12]=[C:11](Br)[C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25]>CN(C=O)C.CCOCC.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([O:14][CH3:15])=[CH:7][C:8]([CH:9]=[O:10])=[C:11]([CH:12]=1)[CH:25]=[CH:24][C:23]([O:27][CH3:28])=[O:26])(=[O:3])[CH3:2]

Participants

8

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 2623485-Bromo-4-formyl-2-methoxyphenyl acetate

Product 1

HCID 53756943Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

Reagents, catalysts & solvents 4

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

To a degassed solution of 4-acetoxy-6-bromo-3-methoxybenzaldehyde (15.4 g), and bis(triphenylphosphine)palladium (11) (1.2 g) in DMF (150 ml) is added triethylamine (31.9 ml) and methyl acrylate (19.6 g). The mixture is heated 135° C. for about 1.5 hours, cooled to room temperature and diluted with ether and water. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by HPLC, eluting with 33% ethyl acetate in hexanes, then methylene chloride, to give the desired product.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by HPLC
  7. washeluting with 33% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6d60ba4013af443b98f7ff64911150e8
Source dataset
uspto-grants-1996_11
Patent number
US05571506

Reaction notes

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