Water → Methyl(4-cyano-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

HRID 591578ノート

反応式

HRID 591578 の反応式
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[C:9]2[C:10]([CH:24]=O)=[CH:11][C:12]([O:14][CH2:15][C:16]3[C:17]([CH3:23])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=3)=[CH:13][C:8]=2[S:7][CH:6]=1.C1COCC1.O.[NH2:33]OS(O)(=O)=O>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[C:9]2[C:10]([C:24]#[N:33])=[CH:11][C:12]([O:14][CH2:15][C:16]3[C:17]([CH3:23])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=3)=[CH:13][C:8]=2[S:7][CH:6]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 8028TetrahydrofuranHCID 76284hydroxylamine-O-sulfonic acidHCID 71721633Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-formyl-1-benzothiophen-3-yl)acetate

生成物 1

HCID 118667069Methyl(4-cyano-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate収率 96.8%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-formyl-1-benzothiophen-3-yl)acetate (100 mg), THF (5 mL) and water (5 mL) was added hydroxylamine-O-sulfonic acid (45.9 mg) at room temperature, and the mixture was refluxed for 48 h. The suspension was diluted with EtOAc, and TEA (1 mL) was added to the mixture. The mixture was refluxed for 1 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (96 mg).

後処理

  1. temperaturethe mixture was refluxed for 48 h
  2. additionwas added to the mixture
  3. temperatureThe mixture was refluxed for 1 h
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed successively with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

出典と根拠

ORDレコード
ord-744cc7cbda9545beaba7fce576530c74
出典データセット
uspto-grants-2016_01
特許番号
US09238639B2

反応ノート

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