3-(2-(6,7-Difluoro-2-quinolinyl)ethenyl)benzaldehyde → 1-(3-(2-(6,7-Difluoro-2-quinolinyl)ethenyl)phenyl)-2-propen-1-ol

HRID 1755775Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH:13]=[CH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19])[CH:6]=[CH:5]2.[CH:23]([Mg]Br)=[CH2:24]>C1(C)C=CC=CC=1.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH:13]=[CH:14][C:15]1[CH:16]=[C:17]([CH:18]([OH:19])[CH:23]=[CH2:24])[CH:20]=[CH:21][CH:22]=1)[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 0 °C

Procedure

The aldehyde of Step 2 (35.93 g, 122 mmol) was suspended in 360 mL of toluene and cooled to 0° C. 1.0 M Vinylmagnesium bromide in THF (135 mL) was added into the addition funnel and the whole system was degassed by applying vacuum and flushed with nitrogen 3 times. The Grignard reagent was then added slowly at 0° C. and the mixture was stirred at 0° C. for 15 min. Cold 25% aq. NH4OAc was then added and the product was extracted in hot toluene, washed with brine, and dried over Na2SO4. The cloudy solution was filtered through celite, concentrated, and filtered through silica with EtOAc: toluene 10:90 to afford 32.04 g (81%) of the title product.

Workup

customthe whole system was degassed
customflushed with nitrogen 3 times
additionThe Grignard reagent was then added slowly at 0° C.
additionCold 25% aq. NH4OAc was then added
extractionthe product was extracted in hot toluene
washwashed with brine
dry with materialdried over Na2SO4
filtrationThe cloudy solution was filtered through celite,
concentrationconcentrated
filtrationfiltered through silica with EtOAc: toluene 10:90

Sources & evidence

ORD record: ord-fb58e4bd95484b5eaa115a04fe51ff4f
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438141

Reaction notes

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