Tri-o-tolylphosphine → HCID 22132398, compound

HRID 1856685Notes

Reaction equation

HRID 1856685 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:23]1[CH2:32][O:31][C:30]2[CH:29]=[CH:28][C:27](Br)=[CH:26][C:25]=2[O:24]1.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][CH2:41][CH:42]([OH:45])[CH:43]=[CH2:44])[CH:35]=1>C(N(CC)CC)C.C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:31]1[C:30]2[CH:29]=[CH:28][C:27]([CH2:44][CH2:43][C:42](=[O:45])[CH2:41][CH2:40][C:36]3[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=3)=[CH:26][C:25]=2[O:24][CH2:23][CH2:32]1.[O:31]1[C:30]2[CH:29]=[CH:28][C:27](/[CH:44]=[CH:43]/[CH:42]([OH:45])[CH2:41][CH2:40][C:36]3[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=3)=[CH:26][C:25]=2[O:24][CH2:23][CH2:32]1

Participants

8

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 1041416-Bromo-1,4-benzodioxaneHCID 17866850HCID 17866850, compound

Product 2

HCID 22132398HCID 22132398, compoundHCID 22132429HCID 22132429, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of palladium(II) acetate (0.112 g), tri-o-tolylphosphine (0.304 g), 3,4-ethylenedioxybromobenzene (1.075 g) and (±)-5-(pyridin-3-yl)-1-penten-3-ol (0.815 g, Example 1a)) in triethylamine (10 ml) in acetonitrile (30 ml) was heated at 80° C. for 3 hours and 30 minutes. The mixture was cooled to room temperature and filtered through Celite® and the filtrate concentrated under reduced pressure. The residue was redissolved in ethyl acetate and the solution washed with water then dried over anhydrous magnesium sulfate. The solution was then filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with hexane:acetone (3:1) then (2:1) to give firstly 1-(benzo-1,4-dioxan-6-yl)-5-(pyridin-3-yl)-3-pentanone as an oil (0.812 g) and secondly (±)-trans-1-(benzo-1,4-dioxan-6-yl)-5-(pyridin-3-yl)-pent-1-en-3-ol as an oil (0.252 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through Celite®
  3. concentrationthe filtrate concentrated under reduced pressure
  4. dissolutionThe residue was redissolved in ethyl acetate
  5. washthe solution washed with water
  6. dry with materialthen dried over anhydrous magnesium sulfate
  7. filtrationThe solution was then filtered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography over silica eluting with hexane:acetone (3:1)

Sources & evidence

ORD record
ord-29f913015d1e467fabab1b28a67e44cd
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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