Diisobutylaluminum hydride → 1-Benzyl-5-chloro-3-hydroxymethylcinnolin-4(1H)-one

HRID 598156ノート

反応式

HRID 598156 の反応式
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([C:20](OC)=[O:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>O1CCCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([CH2:20][OH:21])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 67266995Methyl 1-benzyl-5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate

生成物 1

HCID 672672091-Benzyl-5-chloro-3-hydroxymethylcinnolin-4(1H)-one収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 0.80 g (2.4 mmol) of methyl 1-benzyl-5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate in 50 mL of tetrahydrofuran at −78° C. was added 7.3 mL (7.3 mmol) of DIBAL (1M in tetrahydrofuran). The mixture was allowed to warm to room temperature and stirred for 6 h. The reaction was quenched with 1N HCl and concentrated to a slurry. The slurry was dissolved in dichloromethane and was concentrated onto silica gel. The crude material was purified by flash chromatography eluting with a 4% methanol/dichloromethane mixture to give 0.44 g (60%) of the title compound as a light yellow powder.

後処理

  1. customThe reaction was quenched with 1N HCl
  2. concentrationconcentrated to a slurry
  3. dissolutionThe slurry was dissolved in dichloromethane
  4. concentrationwas concentrated onto silica gel
  5. customThe crude material was purified by flash chromatography
  6. washeluting with a 4% methanol/dichloromethane mixture

出典と根拠

ORDレコード
ord-1e3dbf9531e64d0183b1c3a9f36b6b3b
出典データセット
uspto-grants-2011_03
特許番号
US07897607B2

反応ノート

読み込み中…