Triethylamine → (E)-4-[3-(3-thienyl)phenyl]-3-buten-2-one

HRID 1464765Notes

Reaction equation

HRID 1464765 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:12](O)[CH2:13][C:14](=[O:16])[CH3:15])[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.CS(Cl)(=O)=O.C(N(CC)CC)C>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8](/[CH:12]=[CH:13]/[C:14](=[O:16])[CH3:15])[CH:9]=[CH:10][CH:11]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19917093HCID 19917093, compound

Product 1

HCID 19917181(E)-4-[3-(3-thienyl)phenyl]-3-buten-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The resulting alcohol compound was dissolved in 2 ml of ethyl acetate, and 207 mg of methanesulfonyl chloride and 366 mg of triethylamine were added. The mixture was stirred overnight at room temperature, and then the precipitate was removed by filtration. The filtrate was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=5/1] to give 327 mg of the captioned compound as a pale yellow powder.

Workup

  1. customthe precipitate was removed by filtration
  2. customthe product was purified by silica gel column chromatography [hexane/ethyl acetate=5/1]

Sources & evidence

ORD record
ord-57084c11010c4691b506487f0115ae9a
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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