Methyl 2-hydroxy-7-nitro-2,3-dihydrobenzofuran-4-carboxylate → Methyl 7-nitrobenzofuran-4-carboxylate

HRID 354053ノート

反応式

HRID 354053 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[C:9]2[O:13][CH:12](O)[CH2:11][C:10]=12)=[O:4]>P(=O)(O)(O)O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[C:9]2[O:13][CH:12]=[CH:11][C:10]=12)=[O:4]

参加物

3

反応物 1

HCID 20738652Methyl 2-hydroxy-7-nitro-2,3-dihydrobenzofuran-4-carboxylate

生成物 1

HCID 20738655Methyl 7-nitrobenzofuran-4-carboxylate収率 40%

試薬・触媒・溶媒 1

HCID 1004Phosphoric Acid溶媒

実験手順

2-Hydroxy-7-nitro-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester prepared above was heated in phosphoric acid (60 mL) at 100° C. for one hour. The reaction mixture was poured into ice water and the aqueous solution was extracted with ethyl acetate. The organic phase was washed with brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 15% ethyl acetate in hexane to give 7-nitro-benzofuran-4-carboxylic acid methyl ester as solid (2.3 g, 40%). 1H (CDCl3) δ: 4.04 (s, 3H), 7.54 (d, 1H, J=2.0 Hz), 7.95 (d, 1H, J=1.9 Hz), 8.07 (d, 1H, J=8.5 Hz), 8.17 (d, 1H, J=8.5 Hz).

後処理

  1. extractionthe aqueous solution was extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography over silica gel eluting with 15% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-88add26b2b5b4de4a5f62bbe1580379c
出典データセット
uspto-grants-2004_06
特許番号
US06756395B2

反応ノート

読み込み中…