Triethylamine → HCID 86748446, compound

HRID 274066Notes

Reaction equation

HRID 274066 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=[CH2:16].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:11]=[C:9]1[CH2:10][C:4]2[CH:3]=[C:2](/[CH:16]=[CH:15]/[C:14]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=[CH:12][C:5]=2[CH2:6][CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 200948363-Bromo-5,7,8,9-tetrahydro-6H-benzo[7]annulen-6-one

Product 1

HCID 86748446HCID 86748446, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (2.00 g), ethyl acrylate (1.26 g), palladium acetate (94 mg), tris(2-methylphenyl)phosphine (764 mg), triethylamine (1.69 g) in N,N-dimethylformamide (20 ml) was stirred at 100° C. for 20 hours under nitrogen atmosphere. After cooling, ice water (20 ml) was added to the mixture. The resulting precipitates were collected by filtration and the powder was dissolved in ethyl acetate (20 ml). The solution was washed with water (20 ml) three times, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform as an eluent to give ethyl (E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl)acrylate (1.34 g).

Workup

  1. temperatureAfter cooling
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. dissolutionthe powder was dissolved in ethyl acetate (20 ml)
  5. washThe solution was washed with water (20 ml) three times
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel with chloroform as an eluent

Sources & evidence

ORD record
ord-8d2a3f4a7a6b4c9d95be803056fbb7b5
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

Loading…