Methyl Acrylate → HCID 1474745, compound

HRID 2212047Notes

Reaction equation

HRID 2212047 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]([O:36][CH3:37])(=[O:35])[CH:33]=[CH2:34].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:37][O:36][C:32](=[O:35])/[CH:33]=[CH:34]/[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 813944-Bromophenyl cyclopropyl ketone

Product 1

HCID 1474745HCID 1474745, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of (4-bromophenyl)-(cyclopropyl)methanone (0.450 g, 2.00 mmol), palladium acetate 49 mg, 0.220 mmol), triphenylphosphine (55 mg, 0.21 mmol), methyl acrylate (0.43 g, 2.50 mmol) and triethylamine (10 ml, 72 mmol) was heated to 100° C. for 48 in a closed reaction vial. The reaction mixture was cooled to room temperature. The solid was removed by filtration. A mixture of ice and 1 N hydrochloric acid was added to the liquid. The mixture was stirred for 1 h at room temperature. It was extracted with ethyl acetate (2×150 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g) using a mixture of dichloromethane/ethyl acetate/heptane (1:1:1) as eluent, to give 217 mg of (E)-3-(4-(cyclopropanecarbonyl)phenyl)acrylic acid methyl ester.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solid was removed by filtration
  3. additionA mixture of ice and 1 N hydrochloric acid
  4. additionwas added to the liquid
  5. extractionIt was extracted with ethyl acetate (2×150 ml)
  6. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml)
  7. dry with materialdried over magnesium sulphate
  8. customThe solvent was removed in vacuo
  9. customThe crude product was purified by flash chromatography on silica (40 g)
  10. additiona mixture of dichloromethane/ethyl acetate/heptane (1:1:1) as eluent

Sources & evidence

ORD record
ord-e2aac1089cfd45189cd6646ce92bc719
Source dataset
uspto-grants-2006_09
Patent number
US07101898B2

Reaction notes

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