Dimethyl Sulfoxide → HCID 57284155, compound

HRID 442959Notes

Reaction equation

HRID 442959 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12]([O:15][C:16]1[CH:17]=[C:18]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[O:19][CH2:20][CH2:21][CH2:22][OH:23])(=[O:14])=[O:13].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:4][C:3]=1[S:12]([O:15][C:16]1[CH:17]=[C:18]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[O:19][CH2:20][CH2:21][CH:22]=[O:23])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 57132325HCID 57132325, compound

Product 1

HCID 57284155HCID 57284155, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfur trioxide pyridine complex (720 mg, 4.5 mmol) was added to a solution of 3-[3-(2-chloro-5-trifluoromethylphenylsulfonyloxy)-5-methylphenoxy]propanol (600 mg, 1.4 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.6 mL, 4.7 mmol) and anhydrous dimethyl sulfoxide (0.3 mL, 4.2 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 (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 (410 mg, 69%). 1H-NMR (300 MHz, CDCl3) δ 9.83 (s, 1H), 8.24 (d, J=2.1 Hz, 1H), 7.84 (dd, J=8.4, 2.1 Hz, 1H), 7.78 (d, J=8.4 Hz, 1H), 6.64 (s, 1H), 6.57 (s, 1H), 6.51 (s, 1H), 4.21 (t, J=6.0 Hz, 2H), 2.88 (t, J=6.0 Hz, 2H), 2.27 (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-e9004a656ed446eda0a560ddba57b276
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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