Sodium hydride → Methyl 3-[3-nitro-4-(piperazin-1-yl)phenyl]acrylate

HRID 2378570

反応式

HRID 2378570 の反応式
[Br-].[CH3:2][O:3][C:4]([CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5].[H-].[Na+].[N+:28]([C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[CH:34]=O)([O-:30])=[O:29]>C1COCC1.[Cl-].[Na+].O>[N+:28]([C:31]1[CH:32]=[C:33]([CH:34]=[CH:6][C:4]([O:3][CH3:2])=[O:5])[CH:36]=[CH:37][C:38]=1[N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)([O-:30])=[O:29]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 2733211Phosphonium, (2-methoxy-2-oxoethyl)triphenyl-, bromide (1:1)HCID 607111153-Nitro-4-(piperazin-1-yl)benzaldehyde

生成物 1

HCID 68741140Methyl 3-[3-nitro-4-(piperazin-1-yl)phenyl]acrylate収率 74.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of methoxycarbonylmethyl(triphenyl)phosphonium bromide (1.1 g, TCI) in THF (12.5 ml) was added with sodium hydride (115 mg, WAKO) under ice cooling, warmed to room temperature, then added dropwise with a solution of 3-nitro-4-(piperazin-1-yl)benzaldehyde (550.6 mg, MAYB) in THF (12.5 ml), and stirred at the same temperature for 16.5 hours. The reaction mixture was poured into brine (40 ml), and extracted with ethyl acetate (100 ml). The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (Intermediate Int. n-19, 511 mg).

後処理

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography (hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-ac5ac3ea6cf647ec801334b8c52e1dd3
出典データセット
uspto-grants-2008_12
特許番号
US07470807B2

関連ノート

読み込み中…