p-Anisoyl chloride → HCID 17956193, compound

HRID 346879Notes

Reaction equation

HRID 346879 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:25]=1.[C:26](Cl)(=[O:35])[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1.Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:14][CH:15]=3)=[C:7]([C:26](=[O:35])[C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C:6]=2[CH:25]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 17956195HCID 17956195, compound

Product 1

HCID 17956193HCID 17956193, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Example 4(i) (1 g, 2.8 mmol) in dry DCM was stirred at 0° C. under nitrogen. Anisoyl chloride (4.9 mmol) was added followed by a solution of SnCl4 (1M DCM, 4.9 mmol). An immediate red colour occurred and stirring was continued for 2 hours. The reaction mixture was added carefully to 100 ml of ice-water and the aqueous was extracted with ethylacetate (3×100 Ml). The organic extracts were combined, dried (Na2SO4) and evaporated to give a bright yellow oil. This was purified by flash chromatography (silica flash) to give the title compound as a pale yellow solid. (0.8 g 58%).

Workup

  1. extractionthe aqueous was extracted with ethylacetate (3×100 Ml)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto give a bright yellow oil
  5. customThis was purified by flash chromatography (silica flash)

Sources & evidence

ORD record
ord-976e7131d99e4023b98d49d0274e2994
Source dataset
uspto-grants-2007_02
Patent number
US07173061B2

Reaction notes

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