Triethylamine → HCID 18329179, compound

HRID 1872304Notes

Reaction equation

HRID 1872304 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23]>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:24][C:22](=[CH2:23])[C:21]([O:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1)=[O:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 92203Methyl p-coumarate

Product 1

HCID 18329179HCID 18329179, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

10.5 g (59 mmol) of methyl 3-(4-hydroxy-phenyl)-acrylate were dissolved in 170 ml of tetrahydrofuran and treated in succession with 9.1 ml (65 mmol) of triethylamine and 0.079 g (0.65 mmol) of 4-dimethylamino-pyridine (DMAP). 6.8 g (65 mmol) of methacryloyl chloride were added dropwise to the solution, cooled to about 15° C., over a period of 30 minutes. The reaction batch was stirred at room temperature overnight and subsequently filtered over a thin silica gel layer. The silica gel layer was rinsed thoroughly with THF. After evaporation of the solvent the crude product was recrystallized from about 200 ml of ethanol. It was filtered off, dried and recrystallized once more from ethanol. Filtration and drying at 50° C. in a water-jet vacuum gave 10.3 g of 4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 2-methyl-acrylate as white crystals with a melting point of 76-80° C. and an absorption maximum of λmax. (in CH2Cl2)=281.7 nm (ε=24290 l/mol cm).

Workup

  1. filtrationsubsequently filtered over a thin silica gel layer
  2. washThe silica gel layer was rinsed thoroughly with THF
  3. customAfter evaporation of the solvent the crude product
  4. customwas recrystallized from about 200 ml of ethanol
  5. filtrationIt was filtered off
  6. customdried
  7. customrecrystallized once more from ethanol
  8. filtrationFiltration
  9. dry with materialdrying at 50° C. in a water-jet vacuum

Sources & evidence

ORD record
ord-f7501da74114486eb460881aee7186c4
Source dataset
uspto-grants-2000_08
Patent number
US06107427

Reaction notes

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