Triethylamine → HCID 54268649, compound

HRID 978654Notes

Reaction equation

HRID 978654 reaction equation
I[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([OH:12])[O:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH2:20])=[CH:17][CH:16]=1.CCN(CC)CC>CS(C)=O>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH:20][C:2]2[CH:10]=[C:9]3[C:5]([CH:6]([OH:12])[O:7][C:8]3=[O:11])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 125074-MethoxystyreneHCID 20203477HCID 20203477, compound

Product 1

HCID 54268649HCID 54268649, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.38 g (5 mmol) of 6-iodo-3-hydroxyisobenzofuranone, 0.74 g (5.5 mmol) of p-methoxystyrene, 0.83 ml (5.5 mmol) Et3N, 0.01 g of Pd (OAc)2 and 1 ml of DMSO was prepared in a 10 ml flask. The flask was surmounted with a reflux condenser and the solution was heated to 95° (oil bath) with stirring under N2 for 1 hour. The dark solution was allowed to cool to RT and poured onto 75 ml of ice/H2O with stirring. After standing overnight, the solid which had formed was collected, washed well with cold H2O and air dried. It was then heated with 50 ml of 95% EtOH, charcoaled and filtered. The reddish filtrate was cooled in ice and deposited 100 mg of reddish-brown solid which was found to be impurity and was discarded. The filtrate was evaporated at reduced pressure and the residual orange-yellow solid was triturated with 25 ml of Et2O and filtered to afford 860 mg (60.9%) of the desired coupling product as a yellow solid; homogeneous by TLC--used as is for the next reaction.

Workup

  1. customwas prepared in a 10 ml flask
  2. customThe flask was surmounted with a reflux condenser
  3. temperaturethe solution was heated to 95° (oil bath)
  4. stirringwith stirring
  5. waitAfter standing overnight
  6. customthe solid which had formed
  7. customwas collected
  8. washwashed well with cold H2O and air
  9. customdried
  10. temperatureIt was then heated with 50 ml of 95% EtOH
  11. filtrationfiltered
  12. temperatureThe reddish filtrate was cooled in ice
  13. customThe filtrate was evaporated at reduced pressure
  14. customthe residual orange-yellow solid was triturated with 25 ml of Et2O
  15. filtrationfiltered
  16. customto afford 860 mg (60.9%) of the desired coupling product as a yellow solid
  17. customas is for the next reaction

Sources & evidence

ORD record
ord-0a24b445f67441bdaa9a83ff07878d2a
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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