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

HRID 442946Notes

Reaction equation

HRID 442946 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[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>[Cl:8][C:7]1[CH:2]=[C:3]([S:9]([O:12][C:13]2[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=2)[O:16][CH2:17][CH2:18][CH:19]=[O:20])(=[O:11])=[O:10])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 537073253-[3-(2,3-Dichlorophenylsulfonyloxy)-5-methylphenoxy]propanol

Product 1

HCID 537299203-[3-(3-Chlorophenylsulfonyloxy)-5-methylphenoxy]propionaldehydeYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfur trioxide pyridine complex (480 mg, 4.0 mmol) was added to a solution of 3-[3-(2,3-dichlorophenylsulfonyloxy)-5-methylphenoxy]propanol (460 mg, 1.3 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.5 mL, 3.9 mmol) and anhydrous dimethyl sulfoxide (0.3 mL, 4.2 mmol) in anhydrous dichloromethane (10 mL). The reaction mixture was stirred at ambient temperature for 1 hour and then quenched with 10% aqueous citric acid (50 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 (420 mg, 91%). 1H-NMR (300 MHz, CDCl3) δ 9.84 (s, 1H), 7.86 (s, 1H), 7.74 (d, J=7.9 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.49 (t, J=8.0 Hz, 1H), 6.63 (s, 1H), 6.44 (s, 1H), 6.37 (s, 1H), 4.20 (t, J=6.1 Hz, 2H), 2.87 (t, J=6.1 Hz, 2H), 2.26 (s, 3H).

Workup

  1. customquenched with 10% aqueous citric acid (50 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-73e4b9ca478b4bfc8da6dadbc3b6cd5e
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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