Triethylamine → HCID 86730658, compound

HRID 332873Notes

Reaction equation

HRID 332873 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:12]=[CH:11]/[C:10]([O:14][CH2:15][CH3:16])=[O:13])=[C:3]([CH3:9])[CH:4]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 728574-Bromo-m-cresolHCID 80271Tri-o-tolylphosphine

Product 1

HCID 86730658HCID 86730658, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a microwave vial containing 4-bromo-3-methylphenol (600 mg, 3.21 mmol) in anhydrous DMF (3.0 mL) was added ethyl acrylate (996 mg, 9.94 mmol), palladium (II) acetate (72.0 mg, 0.321 mmol), tri(o-tolyl)phosphine (146 mg, 0.481 mmol) and triethylamine (1.57 mL, 11.23 mmol). The resulting mixture was sealed and subjected to microwave irridation at 120° C. for 2 h after which time the reaction was diluted with EtOAc and filtered through Celite™. The filtrate was then washed with water, brine and dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the crude product as a brown oil which was purified by column chromatography (SiO2, 0-30% EtOAc/Heptane) to afford (E)-ethyl 3-(4-hydroxy-2-methylphenyl)acrylate (289.8 mg, 1.405 mmol, 44% yield). LC/MS (m/z, MH+): 207.2.

Workup

  1. customThe resulting mixture was sealed
  2. customat 120° C.
  3. customfor 2 h
  4. filtrationfiltered through Celite™
  5. washThe filtrate was then washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude product as a brown oil which
  10. customwas purified by column chromatography (SiO2, 0-30% EtOAc/Heptane)

Sources & evidence

ORD record
ord-981c9a7d1aca4bb3ac9dde278263a17a
Source dataset
uspto-grants-2014_11
Patent number
US08877801B2

Reaction notes

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