(2-(Dimethylamino)ethyl)triphenylphosphonium bromide → (E)-3-[4-(3-Dimethylaminopropenyl)phenyl]acrylic Acid

HRID 1637885Notes

Reaction equation

HRID 1637885 reaction equation
[Br-].[CH3:2][N:3]([CH3:25])[CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH:36]([C:38]1[CH:43]=[CH:42][C:41]([CH:44]=[CH:45][C:46]([O:48][CH3:49])=[O:47])=[CH:40][CH:39]=1)=O>CN(C=O)C>[CH3:2][N:3]([CH3:25])[CH2:4][CH:5]=[CH:36][C:38]1[CH:43]=[CH:42][C:41](/[CH:44]=[CH:45]/[C:46]([O:48][CH3:49])=[O:47])=[CH:40][CH:39]=1.[CH3:2][N:3]([CH3:25])[CH2:4][CH:5]=[CH:36][C:38]1[CH:43]=[CH:42][C:41](/[CH:44]=[CH:45]/[C:46]([OH:48])=[O:47])=[CH:40][CH:39]=1

Participants

6

Reactant 3

HCID 2724136(2-(Dimethylamino)ethyl)triphenylphosphonium bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 53401287Methyl 3-(4-formylphenyl)-2-propenoate

Product 2

HCID 70098974(E)-3-[4-(3-Dimethylaminopropenyl)phenyl]acrylic AcidYield 34%HCID 86755260(E)-3-[4-(3-dimethylaminopropenyl)phenyl]acrylic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-3-[4-(3-Dimethylaminopropenyl)phenyl]acrylic acid, methyl ester was prepared by the following way: (2-dimethylaminoethyl)triphenylphosphonium bromide (7.2 g, 17.4 mmol) in 30 mL of DMF was treated with KHMDS (27 mL, 1.01 equiv., 0.5 M in toluene) at -78° C. for one hour. At -40° C., 3-(4-formylphenyl)acrylic acid, methyl ester (2.54 g, 13.3 mmol, prepared according to the procedure of Syper et al., Synthesis, 1984, 9, 747-752) was added dropwise. The resulting mixture was stirred for 12 hours at rt and quenched with water. Extraction with EtOAc, drying over MgSO4 and evaporation in vacuo gave a residue that was purified via flash chromatography with DCM:MeOH (90:10) as eluting solvent. The title compound (1.1 g, 34%) was obtained as an orange oil.

Workup

  1. customaccording to the procedure of Syper et al., Synthesis, 1984, 9, 747-752)
  2. additionwas added dropwise
  3. customquenched with water
  4. extractionExtraction with EtOAc
  5. dry with materialdrying over MgSO4 and evaporation in vacuo
  6. customgave a residue that
  7. customwas purified via flash chromatography with DCM:MeOH (90:10)
  8. washas eluting solvent

Sources & evidence

ORD record
ord-87718733d0ef42998d8014a62451a771
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

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