Methyl Acrylate → HCID 21841221, compound

HRID 1739499Notes

Reaction equation

HRID 1739499 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:6]=[CH:5]2.C(N(CC)CC)C.[C:27]([O:31][CH3:32])(=[O:30])[CH:28]=[CH2:29].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[OH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2](/[CH:29]=[CH:28]/[C:27]([O:31][CH3:32])=[O:30])[CH:11]=[CH:10]2

Participants

8

Reactant 4

HCID 7294Methyl Acrylate2×HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 22709072HCID 22709072, compound

Product 1

HCID 21841221HCID 21841221, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.2 g of 6-bromo-2-(6-hydroxyhexyloxy)naphthalene, 25 ml of triethylamine, 4.3 ml of methyl acrylate, 0.072 g of palladium acetate and 0.392 g of tri-o-tolylphosphine was heated under reflux for 16 hrs. In order to complete the reaction, a further 0.177 g of palladium acetate, 2.5 g of tetrabutylammonium bromide, 10 ml of dimethylformamide and 2 ml of methyl acrylate were added and the mixture was heated to reflux for a further 24 hrs. Thereafter, the reaction mixture was cooled, partitioned between ethyl acetate and water, the organic phase was washed with water, and dried over magnesium sulphate, filtered and evaporated. The residue was chromatographed on 250 g of silica gel with toluene/ethyl acetate (3:1 to 1:1) and subsequently crystallized twice from toluene. This gave 0.63 g of methyl (E)-3-[6-(6-hydroxyhexyloxy)naphthalen-2-yl]acrylate as a colorless solid, λmax. (CH2Cl2): 326 nm (ε=27660).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hrs
  3. customthe reaction
  4. temperaturethe mixture was heated
  5. temperatureto reflux for a further 24 hrs
  6. temperatureThereafter, the reaction mixture was cooled
  7. custompartitioned between ethyl acetate and water
  8. washthe organic phase was washed with water
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was chromatographed on 250 g of silica gel with toluene/ethyl acetate (3:1 to 1:1)
  13. customsubsequently crystallized twice from toluene

Sources & evidence

ORD record
ord-ba98aca8e20d40098b56ae5b004c7d0a
Source dataset
uspto-grants-1999_10
Patent number
US05965761

Reaction notes

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