Dimethyl Sulfoxide → 3-[3-(5-Isoquinolinylsulfonyloxy)-5-methylphenoxy]propionaldehyde

HRID 442969Notes

Reaction equation

HRID 442969 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([O:14][C:15]3[CH:16]=[C:17]([CH:23]=[C:24]([CH3:26])[CH:25]=3)[O:18][CH2:19][CH2:20][CH2:21][OH:22])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([O:14][C:15]3[CH:16]=[C:17]([CH:23]=[C:24]([CH3:26])[CH:25]=3)[O:18][CH2:19][CH2:20][CH:21]=[O:22])(=[O:12])=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 227225083-[3-(5-Isoquinolinylsulfonyloxy)-5-methylphenoxy]propanol

Product 1

HCID 539207413-[3-(5-Isoquinolinylsulfonyloxy)-5-methylphenoxy]propionaldehydeYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfur trioxide pyridine complex (240 mg, 1.5 mmol) was added to a solution of 3-[3-(5-isoquinolinylsulfonyloxy)-5-methylphenoxy]propanol (190 mg, 0.5 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.2 mL, 1.6 mmol) and anhydrous dimethyl sulfoxide (0.1 mL, 1.4 mmol) in anhydrous dichloromethane (20 mL). The reaction mixture was stirred at ambient temperature for 1 hour and then quenched with 10% aqueous citric acid (30 mL). The mixture was extracted into dichloromethane (3×30 mL), and the dichloromethane solution was washed with 10% aqueous citric acid (30 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (3:1 ethyl acetate/dichloromethane) to give the title compound as a colorless oil (135 mg, 72%). 1H-NMR (300 MHz, CDCl3) δ 9.79 (s, 1H), 9.46 (s, 1H), 8.80 (d, J=6.2 Hz, 1H), 8.59 (d, J=5.8 Hz, 1H), 8.37 (d, J=7.5 Hz, 1H), 8.34 (d, J=8.3 Hz, 1H), 7.71 (t, J=7.7 Hz, 1H), 6.56 (s, 1H), 6.32 (s, 1H), 6.24 (s, 1H), 4.09 (t, J=6.0 Hz, 2H), 2.81 (t, J=6.0 Hz, 2H), 2.17 (s, 3H).

Workup

  1. customquenched with 10% aqueous citric acid (30 mL)
  2. extractionThe mixture was extracted into dichloromethane (3×30 mL)
  3. washthe dichloromethane solution was washed with 10% aqueous citric acid (30 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent in vacuo
  6. customthe residue was purified by flash column chromatography (3:1 ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-bfa31207af634900b5627f067ac95eaf
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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