Methyl Acrylate → Methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]acrylate

HRID 1181586Notes

Reaction equation

HRID 1181586 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][CH2:11][C@H:12]1[CH2:14][O:13]1)[CH3:9].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[C:44]([O:48][CH3:49])(=[O:47])[CH:45]=[CH2:46]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:13]1[CH2:14][C@@H:12]1[CH2:11][O:10][C@@H:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:46]=[CH:45][C:44]([O:48][CH3:49])=[O:47])[CH3:9]

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 58981243(2R)-2-[[(1R)-1-(2-bromophenyl)ethoxy]methyl]oxirane

Product 1

HCID 86605593Methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]acrylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

(2R)-2-[[(1R)-1-(2-Bromophenyl)ethoxy]methyl]oxirane (1.00 g) obtained in Step 1 was dissolved in acetonitrile (10 ml), palladium acetate (II) (45 mg), tri-o-tolylphosphine (63 mg), triethylamine (0.65 ml) and methyl acrylate (0.42 ml) were added, and the mixture was heated under reflux for 3 hr. The reaction mixture was cooled to room temperature, and, after filtration through celite, concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the title compound (203 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. filtrationafter filtration through celite
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-517279658158461ba169ac01b7303e4f
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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