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

HRID 1497557ノート

反応式

HRID 1497557 の反応式
[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

参加物

6

反応物 3

HCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 90282113Benzyl 6-(benzyloxy)quinoline-2-carboxylate

生成物 1

HCID 902819596-(Benzyloxy)quinoline-2-carbaldehyde収率 36.7%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-41cbf27534be47d4b13c5eb0206cb237
出典データセット
uspto-grants-2015_12
特許番号
US09199927B2

反応ノート

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