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

HRID 1004117

Reaction equation

HRID 1004117 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-279192533af44176973fc9428f9f238f
Source dataset
uspto-grants-2000_04
Patent number
US06048875

Linked notes

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