Dimethyl Sulfoxide → 3-[3-(2,5-Dimethylphenylsulfonyloxy)-5-methylphenoxy]propionaldehyde

HRID 442938Notes

Reaction equation

HRID 442938 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH2:19][OH:20])(=[O:11])=[O:10].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH:19]=[O:20])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 539991233-[3-(2,5-Dimethylphenylsulfonyloxy)-5-methylphenoxy]propanol

Product 1

HCID 542818573-[3-(2,5-Dimethylphenylsulfonyloxy)-5-methylphenoxy]propionaldehydeYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfur trioxide pyridine complex (800 mg, 5.0 mmol) was added to a solution of 3-[3-(2,5-dimethylphenylsulfonyloxy)-5-methylphenoxy]propanol (600 mg, 1.7 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.7 mL, 5.5 mmol) and anhydrous dimethyl sulfoxide (0.4 mL, 5.6 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 (60 mL). The mixture was extracted into dichloromethane (3×50 mL), and the dichloromethane solution was washed with 10% aqueous citric acid (40 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane) to give the title compound as a colorless oil (530 mg, 89%). 1H-NMR (300 MHz, CDCl3) δ 9.82 (s, 1H), 7.68 (s, 1H), 7.33 (d, J=7.8 Hz, 1H), 7.29 (s, 1H), 6.60 (s, 1H), 6.45 (s, 1H), 6.35 (s, 1H), 4.17 (t, J=6.1 Hz, 2H), 2.85 (t, J=6.1 Hz, 2H), 2.70 (s, 3H), 2.33 (s, 3H), 2.24 (s, 3H).

Workup

  1. customquenched with 10% aqueous citric acid (60 mL)
  2. extractionThe mixture was extracted into dichloromethane (3×50 mL)
  3. washthe dichloromethane solution was washed with 10% aqueous citric acid (40 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent in vacuo
  6. customthe residue was purified by flash column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-ffad1ceb528243328c5d0425d6821cf5
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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