Methyl Acrylate → Methyl (E)-3-(6-heptyloxynaphth-2-yl)acrylate

HRID 650850Notes

Reaction equation

HRID 650850 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][CH3:19])[CH:6]=[CH:5]2.[C:20]([O:24][CH3:25])(=[O:23])[CH:21]=[CH2:22].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH2:13]([O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2](/[CH:22]=[CH:21]/[C:20]([O:24][CH3:25])=[O:23])[CH:11]=[CH:10]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 106157136-Bromo-2-heptyloxynaphthalene

Product 1

HCID 21182539Methyl (E)-3-(6-heptyloxynaphth-2-yl)acrylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 5.2 g of 6-bromo-2-heptyloxynaphthalene, 25 ml of triethylamine, 4.3 ml of methyl acrylate, 0.072 g of palladium acetate and 0.392 g of tri-o-tolylphosphine is refluxed for 16 hours. The reaction mixture is then cooled and is partitioned between ethyl acetate and water and the organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated down. The residue is chromatographed over 250 g of silica gel using toluene/ethyl acetate (3:1) and then crystallized from toluene. This gives methyl (E)-3-(heptyloxynaphth-2-yl)acrylate.

Workup

  1. temperatureis refluxed for 16 hours
  2. temperatureThe reaction mixture is then cooled
  3. customis partitioned between ethyl acetate and water
  4. washthe organic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated down
  8. customThe residue is chromatographed over 250 g of silica gel
  9. customcrystallized from toluene

Sources & evidence

ORD record
ord-66da3151daeb4fe9bf4d1e312a52499b
Source dataset
uspto-grants-2001_08
Patent number
US06277502B1

Reaction notes

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