5-tert-Butylsalicylaldehyde → HCID 7172095、化合物

HRID 1787453ノート

反応式

HRID 1787453 の反応式
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].[O:14]=[N+:15]=[O:16]>CC#N>[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:16])=[O:14])[C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 14750905-tert-ButylsalicylaldehydeHCID 3609161Nitronium

生成物 1

HCID 7172095HCID 7172095、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 15.0 g (84.2 mmol) of 5-tert-Butyl-2-hydroxy-benzaldehyde in MeCN at −30° C. was added 14.5 g (109.4 mmol) of nitronium tetrafluoborate. The temperature was allowed to climb slowly to −12° C. ove 1 h. The mixture was partitioned between sat'd NaHCO3 and EtOAc. The organic layer was washed with water and brine then dried over MgSO4. After filtration and evaporation, 5-tert-butyl-2-hydroxy-3-nitro-benzaldehyde was obtained as yellow solid. To a portion of this material (6.27 g, 28.1 mmol) in 40 mL of DMF was added 19.4 g of K2CO3 in two batches. To this slurry was added 6.12 mL (98.3 mmol) of MeI. The mixture was stirred overnight, filtered, and diluted with EtOAc. This mixture was washed with water, and the wash was then extracted with EtOAc (3×150 mL). The extracts were washed with water and brine, then dried over MgSO4, filtered, and concentrated. Chromatography (5% EtOAc in hexanes) provided 5.38 g of 5-tert-butyl-2-methoxy-3-nitro-benzaldehyde as an off-white solid.

後処理

  1. customThe mixture was partitioned between sat'd NaHCO3 and EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialthen dried over MgSO4
  4. filtrationAfter filtration and evaporation

出典と根拠

ORDレコード
ord-a36399ed97d24ce9a1f6250089cbfde6
出典データセット
uspto-grants-2009_03
特許番号
US07511042B2

反応ノート

読み込み中…