Diisobutylaluminum hydride → HCID 86614859、化合物

HRID 2198077ノート

反応式

HRID 2198077 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:5](N(OC)C)=[O:6].[CH3:17][CH:18](C[AlH]CC(C)C)C>C1COCC1.Cl.CCOC(C)=O>[CH2:17]([C:3]1[C:2]([F:1])=[C:13]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:11][C:4]=1[CH:5]=[O:6])[CH3:18]

参加物

6

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 577580833-Fluoro-N-methoxy-N-methyl-4-nitrobenzamide

生成物 1

HCID 86614859HCID 86614859、化合物収率 88%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of THF (800 mL) cooled in an ice-salt/water bath was added 3-fluoro-N-methoxy-N-methyl-4-nitrobenzamide followed by addition of 1 M DIBAL in THF by addition funnel over 30 min. The solution was allowed to stir under N2 for 1 h. The reaction mixture was then carefully diluted with 1N HCl (500 mL) and EtOAc (500 mL), transferred to separatory funnel, and separated. The organic phase was washed with 1N HCl (3×250 mL), 1N NaOH (2×250 mL), and water (250 mL). All aqueous layers were back extracted with EtOAc (2×250 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated in vacuo to afford 67 g of the above compound (396 mmol, yield 88%). 1H-NMR (DMSO-d6) 10.06 (s, 1H), 8.36 to 8.32 (t, J=7.8 Hz, 1H), 8.06 to 8.03 (d, J=11.2 Hz, 1H), 7.95 to 7.93 (d, J=9.1 Hz, 1H).

後処理

  1. customtransferred to separatory funnel
  2. customseparated
  3. washThe organic phase was washed with 1N HCl (3×250 mL), 1N NaOH (2×250 mL), and water (250 mL)
  4. extractionAll aqueous layers were back extracted with EtOAc (2×250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-535b5f84d9db4a829b85cca5fd263d21
出典データセット
uspto-grants-2012_12
特許番号
US08338595B2

反応ノート

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