1,3-Propanediol → 2,2-dimethyl-2H-pyrano[2,3-g]quinoline

HRID 1993490Notes

Reaction equation

HRID 1993490 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH:6]=[CH:5]2.[CH2:14](O)[CH2:15][CH2:16]O.C(P(CCCC)CCCC)CCC>COCCOC.[Ru](Cl)(Cl)Cl>[CH3:12][C:7]1([CH3:13])[O:8][C:9]2=[CH:10][C:11]3[CH:14]=[CH:15][CH:16]=[N:1][C:2]=3[CH:3]=[C:4]2[CH:5]=[CH:6]1

Participants

6

Reactant 3

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 100808812,2-Dimethyl-2H-chromen-6-amine

Product 1

HCID 591344202,2-dimethyl-2H-pyrano[2,3-g]quinolineYield 59%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
180 °C

Procedure

Under nitrogen atmosphere, to a solution of 6-amino-2,2-dimethylchromene (3.88 g, 22.1 mmol) and ruthenium trichloride (55.0 mg, 0.265 mmol) in dimethylene glycol dimethyl ether (8 mL), 1,3-propanediol (0.639 mL, 8.84 mmol) and tri-n-butyl phosphine (0.132 mL, 0.530 mmol) were addled at room temperature, and the resulting mixture was stirred at 180° C. for 5 hours. Upon the completion of the reaction, ruthenium complex was removed by florisil column, and solvent was distilled off. The residue was purified by medium pressure column chromatography (hexane/ethyl acetate=5/1) and the aimed product was obtained (yield: 59%).

Workup

  1. customwere addled at room temperature
  2. customUpon the completion of the reaction, ruthenium complex
  3. customwas removed by florisil column, and solvent
  4. distillationwas distilled off
  5. customThe residue was purified by medium pressure column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-3f84d804e0b9443b808ecafe579ed441
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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