Acetic Anhydride → Ethyl (E)-3-[5,6-dimethoxy-3-(4-methoxyphenoxy)benzo[b]thiophen-2-yl]-2-(4-pyridinyl)-2-propenoate

HRID 1004117

反応式

HRID 1004117 の反応式
[CH3:1][O:2][C:3]1[C:22]([O:23][CH3:24])=[CH:21][C:6]2[S:7][C:8]([CH:19]=O)=[C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[C:5]=2[CH:4]=1.[N:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:27][CH:26]=1.C(OC(=O)C)(=O)C.C([O-])(O)=O.[Na+]>>[CH3:1][O:2][C:3]1[C:22]([O:23][CH3:24])=[CH:21][C:6]2[S:7][C:8](/[CH:19]=[C:31](\[C:28]3[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=3)/[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:9]([O:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[C:5]=2[CH:4]=1

参加物

5

反応物 4

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 736321Ethyl pyridine-4-acetateHCID 110892155,6-Dimethoxy-3-(4-methoxyphenoxy)benzo[b]thiophene-2-carbaldehyde

生成物 1

HCID 86755303Ethyl (E)-3-[5,6-dimethoxy-3-(4-methoxyphenoxy)benzo[b]thiophen-2-yl]-2-(4-pyridinyl)-2-propenoate

反応条件

温度
100 °C

実験手順

A solution containing 6 mmol of the product obtained in Step E, 30 mmol of ethyl 4-pyridylacetate and 5 ml of acetic anhydride is maintained at 100° C. for 18 hours. After returning to room temperature, the reaction mixture is hydrolysed by a saturated NaHCO3 solution and extracted with ethyl acetate. The organic phases are then washed with water and then with an NaCl solution, dried over calcium sulphate, filtered and concentrated under reduced pressure. Chromatography over silica gel (dichloromethane/ethanol: 98/2) enables the expected product to be isolated.

後処理

  1. customAfter returning to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phases are then washed with water
  4. dry with materialwith an NaCl solution, dried over calcium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto be isolated

出典と根拠

ORDレコード
ord-279192533af44176973fc9428f9f238f
出典データセット
uspto-grants-2000_04
特許番号
US06048875

関連ノート

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