Dimethyl Sulfoxide → 3-[5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenoxy]propionaldehyde

HRID 442949Notes

Reaction equation

HRID 442949 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:13][S:14]([C:17]2[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=2[CH3:26])(=[O:16])=[O:15])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][CH2:9][CH2:10][OH:11].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([O:13][S:14]([C:17]2[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=2[CH3:26])(=[O:16])=[O:15])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][CH2:9][CH:10]=[O:11]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 537902373-[5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenoxy]propanol

Product 1

HCID 543965433-[5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenoxy]propionaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfur trioxide pyridine complex (960 mg, 6.0 mmol) was added to a solution of 3-[5-methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenoxy]propanol (760 mg, 2.0 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 (70 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 (590 mg, 78%). 1H-NMR (300 MHz, CDCl3) δ 9.83 (s, 1H), 8.72 (s, 1H), 8.38 (d, J=8.4 Hz, 1H), 7.63 (d, J=8.4 Hz, 1H), 6.63 (s, 1H), 6.46 (s, 1H), 6.39 (s, 1H), 4.21 (t, J=6.0 Hz, 2H), 2.89 (s, 3H), 2.87 (t, J=6.0 Hz, 2H), 2.26 (s, 3H).

Workup

  1. customquenched with 10% aqueous citric acid (70 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-4e292a6dae364bf5b769d21922191eba
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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