Allyl Alcohol → 3-(Quinolin-6-yl)propanal

HRID 500119Notes

Reaction equation

HRID 500119 reaction equation
F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.Br[C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[CH:25][CH:24]=[CH:23]2.[CH2:30]([OH:33])[CH:31]=[CH2:32].C1(N(C)C2CCCCC2)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[N:26]1[C:27]2[C:22](=[CH:21][C:20]([CH2:32][CH2:31][CH:30]=[O:33])=[CH:29][CH:28]=2)[CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 7858Allyl AlcoholHCID 24210N-Methyl dicyclohexylamineHCID 792436-BromoquinolineHCID 2734635Tri-tert-butylphosphine tetrafluoroborate

Product 1

HCID 229313103-(Quinolin-6-yl)propanal

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
30 °C

Procedure

Tris(dibenzylideneacetone)dipalladium (480 mg, 0.52 mmol) and tri-tert-butyl-phosphonium tetrafluoroborate (300 mg, 1.0 mmol) in a flask was evacuated and refilled with nitrogen (2 times). 1,4-dioxane (31 mL) was added followed by consecutive addition of 6-bromoquinoline (7.2 g, 35 mmol), 2-propen-1-ol (4.7 mL, 69 mmol) and N-cyclohexyl-N-methyl-cyclohexanamine (8.9 mL, 42 mmol). The reaction vessel was evacuated and refilled with nitrogen (2 times). The reaction mixture was stirred at 30° C. for 24 h. Diethyl ether (30 mL) was added to the reaction mixture and then filtered and washed with diethyl ether. The organic extract was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate in hexanes (0-50%) to afford the desired product. (˜55%) LCMS: (M+H)=186.0; (M+H2O+H)+=204.0.

Workup

  1. additionrefilled with nitrogen (2 times)
  2. customThe reaction vessel was evacuated
  3. additionrefilled with nitrogen (2 times)
  4. additionDiethyl ether (30 mL) was added to the reaction mixture
  5. filtrationfiltered
  6. washwashed with diethyl ether
  7. extractionThe organic extract
  8. concentrationwas concentrated under reduced pressure
  9. customThe residue was purified by flash chromatography
  10. washeluting with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-24536ae232894713aeee402874c273f5
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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