3-[(E)-2-(7-Chloroquinolin-2-yl)ethenyl]benzaldehyde → 1-{3-[(E)-2-(7-Chloroquinolin-2-yl)ethenyl]phenyl}ethan-1-ol

HRID 1198563Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=[O:18])=[N:9]2)=[CH:4][CH:3]=1.[CH3:22][Mg]I>C1COCC1.C(OCC)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:17]([OH:18])[CH3:22])[CH:19]=[CH:20][CH:21]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-[2(E)-(7-Chloroquinolin-2-yl)ethenyl}benzaldehyde (Example 6a part i) (2.44 g, 8.3 mmol) in dry THF (75 ml) was cooled in an ice bath under nitrogen and stirred as 1M methyl magnesium iodide in diethyl ether (9.9 ml) was added over 5 minutes. The reaction was stirred at 0° C. for half an hour, warmed to room temperature and quenched with water. The mixture was extracted into ethyl acetate, the combined organic extracts dried, filtered and evaporated in vacuo.

Workup

additionwas added over 5 minutes
temperaturewarmed to room temperature
customquenched with water
extractionThe mixture was extracted into ethyl acetate
customthe combined organic extracts dried
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-9e081498f58c443e8b1e09b11ceed6db
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05281593

Reaction notes

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