Sodium sulfate decahydrate → 6-(Benzyloxy)quinoline-2-carbaldehyde

HRID 1497557Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19](OCC1C=CC=CC=1)=[O:20])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH:19]=[O:20])[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of benzyl 6-(benzyloxy)quinoline-2-carboxylate (650 mg) in tetrahydrofuran (13.0 mL) was added a 1 M solution diisobutylaluminum hydride in toluene (2.64 mL) at −78° C., followed by stirring at −78° C. for 1 hour. To the reaction mixture was added sodium sulfate decahydrate (680 mg), followed by stirring at room temperature overnight. The insoluble material was collected by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 6-(benzyloxy)quinoline-2-carbaldehyde (170 mg).

Workup

stirringby stirring at room temperature overnight
filtrationThe insoluble material was collected by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-41cbf27534be47d4b13c5eb0206cb237
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199927B2

Reaction notes

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