Dimethyl Sulfoxide → 1-(3-Methoxy-4-pyridin-2-ylphenyl)propan-1-one

HRID 2213108Notes

Reaction equation

HRID 2213108 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]([OH:18])[CH2:16][CH3:17])[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.CS(C)=O.CCN(CC)CC>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15](=[O:18])[CH2:16][CH3:17])[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 21956527HCID 21956527, compound

Product 1

HCID 219565211-(3-Methoxy-4-pyridin-2-ylphenyl)propan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-ol (134 mg, 0.55 mmol) was dissolved in CH2Cl2 (3 mL), DMSO (0.5 mL), Et3N (0.5 mL) and was treated with sulfur trioxide pyridine complex (350 mg, 2.2 mmol) at 0° C. for 12 h. The reaction mixture was diluted with water (10 mL) and the product was extracted into CH2Cl2 (3×10 mL), dried (MgSO4), concentrated and purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 1:1) to afford 1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-one.

Workup

  1. extractionthe product was extracted into CH2Cl2 (3×10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 1:1)

Sources & evidence

ORD record
ord-b10fbefb4f33408aba09c57901707070
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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