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

HRID 354053노트

반응식

HRID 354053 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

HCID 20738655Methyl 7-nitrobenzofuran-4-carboxylate수율 40%

시약·촉매·용매 1

HCID 1004Phosphoric Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-88add26b2b5b4de4a5f62bbe1580379c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756395B2

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