Methyl Acrylate → HCID 58907415, compound

HRID 1985994Notes

Reaction equation

HRID 1985994 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:11]=[C:9]([CH3:10])[CH2:8][C:4]1[CH:3]=[C:2](/[CH:14]=[CH:13]/[C:12]([O:16][CH3:17])=[O:15])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 27340931-(3-Bromophenyl)propan-2-one

Product 1

HCID 58907415HCID 58907415, compoundYield 105.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 3-bromophenylacetone (50.0 g, 235 mmol), methyl acrylate (40.4 g, 469 mmol), palladium(II) acetate (7.9 g, 35.2 mmol), tri-ortho-tolylphosphine (21.4 g, 70.4 mmol) and triethylamine (82 mL) in acetonitrile (900 mL) was heated at reflux under a nitrogen atmosphere for 16 hours. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. Purification by flash column chromatography eluting with pentane:ethyl acetate 90:10 to 70:30 gave the title compound as an orange oil (54.3 g). 1H NMR (400 MHz, CD3OD) δ: 2.15 (3H, s), 3.70 (2H, s), 3.77 (3H, s), 6.43-6.39 (1H, d), 7.20-7.18 (1H, d), 7.34-7.31 (2H, t), 7.41-7.39 (1H, d), 7.66-7.62 (1H, d); LRMS ESI m/z 241 [M+Na]+, 217 [M−H]−.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 16 hours
  2. customthe solvent removed in vacuo
  3. customPurification by flash column chromatography
  4. washeluting with pentane:ethyl acetate 90:10 to 70:30

Sources & evidence

ORD record
ord-d42c0996f205463cba2d98c1c0f0961a
Source dataset
uspto-grants-2009_06
Patent number
US07547731B2

Reaction notes

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