Dimethyl Sulfoxide → HCID 54268437, compound

HRID 442978Notes

Reaction equation

HRID 442978 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([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][CH2:19][OH:20])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 54020412HCID 54020412, compound

Product 1

HCID 54268437HCID 54268437, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfur trioxide pyridine complex (1.10 g, 7.0 mmol) was added to a solution of 3-[3-(3-cyanophenylsulfonyloxy)-5-methylphenoxy]propanol (1.05 g, 3.0 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 (80 mL). The mixture was extracted into dichloromethane (3×60 mL), and the dichloromethane solution was washed with 10% aqueous citric acid (50 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 (770 mg, 74%). 1H-NMR (300 MHz, CDCl3) δ 9.84 (s, 1H), 8.14 (s, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.72 (t, J=7.9 Hz, 1H), 6.65 (s, 1H), 6.42 (s, 1H), 6.37 (s, 1H), 4.21 (t, J=6.0 Hz, 2H), 2.89 (t, J=6.0 Hz, 2H), 2.27 (s, 3H).

Workup

  1. customquenched with 10% aqueous citric acid (80 mL)
  2. extractionThe mixture was extracted into dichloromethane (3×60 mL)
  3. washthe dichloromethane solution was washed with 10% aqueous citric acid (50 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-571202c9cbbf4b4db65013ed5e3bdfb5
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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