Methoxyacetic Acid → 7-Benzyloxy-3-methoxy-6-nitrochromen-2-one

HRID 643949ノート

反応式

HRID 643949 の反応式
[CH3:1][O:2][CH2:3][C:4]([O-:6])=[O:5].[Na+].COCC(O)=O.[OH-].[Na+].COCC(Cl)=O.[CH2:22]([O:29][C:30]1[C:37]([N+:38]([O-:40])=[O:39])=[CH:36][C:33]([CH:34]=O)=[C:32](O)[CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CCO.CN(C=O)C.CCOC(C)=O>[CH2:22]([O:29][C:30]1[CH:31]=[C:32]2[C:33]([CH:34]=[C:3]([O:2][CH3:1])[C:4](=[O:6])[O:5]2)=[CH:36][C:37]=1[N+:38]([O-:40])=[O:39])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

9

反応物 5

HCID 12251Methoxyacetic AcidHCID 14798Sodium HydroxideHCID 96623Methoxyacetyl chlorideHCID 4114130Acetic acid, 2-methoxy-, sodium salt (1:1)HCID 866240244-Benzyloxy-2-hydroxy-5-nitrobenzaldehyde

生成物 1

HCID 866240257-Benzyloxy-3-methoxy-6-nitrochromen-2-one

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Sodium methoxyacetate (0.739 g, 6.6 mmol), prepared from methoxyacetic acid and NaOH in EtOH, is dissolved in 3.3 mL of DMF and cooled to 0° C. Methoxyacetyl chloride (0.39 mL, 4.0 mmol) is added dropwise. The mixture is stirred for 15 min at ambient temperature. 4-Benzyloxy-2-hydroxy-5-nitrobenzaldehyde (0.360 g, 1.32 mmol) is added and the solution refluxed for 3 h. After cooling to ambient temperature, EtOAc is added and the mixture is washed with 10% aqueous HCl, water, and sat. NaCl, then dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by recrystallization from EtOAc to afford 7-benzyloxy-3-methoxy-6-nitrochromen-2-one as a yellow solid: mp=226-228° C.; 1H NMR (DMSO-d6) δ 8.27 (s, 1H), 7.48-7.35 (m, 7H), 5.36 (s, 2H), 3.82 (s, 3H); (M−H)−=326.

後処理

  1. temperaturethe solution refluxed for 3 h
  2. temperatureAfter cooling to ambient temperature
  3. washthe mixture is washed with 10% aqueous HCl, water, and sat. NaCl
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue purified by recrystallization from EtOAc

出典と根拠

ORDレコード
ord-9d10029bf9c74eb4a2b893fceae00f95
出典データセット
uspto-grants-2010_04
特許番号
US07700633B2

反応ノート

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