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

HRID 1257779Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH2:12]([OH:15])[CH:13]=[CH2:14].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:8]1[C:9]2[C:4](=[CH:3][C:2]([CH2:14][CH2:13][CH:12]=[O:15])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 30 °C

Procedure

Tris(dibenzylideneacetone)dipalladium (480 mg, 0.52 mmol) and tri-tent-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

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

Sources & evidence

ORD record: ord-ee685dfa0a374089ba26f4a8a9c13d41
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461330B2

Reaction notes

Loading…