Dimethyl Sulfoxide → HCID 57208440, compound

HRID 442965Notes

Reaction equation

HRID 442965 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[S:10]([O:13][C:14]1[CH:15]=[C:16]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[O:17][CH2:18][CH2:19][CH2:20][OH:21])(=[O:12])=[O:11])#[N:2].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[S:10]([O:13][C:14]1[CH:15]=[C:16]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[O:17][CH2:18][CH2:19][CH:20]=[O:21])(=[O:12])=[O:11])#[N:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 53819816HCID 53819816, compound

Product 1

HCID 57208440HCID 57208440, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfur trioxide pyridine complex (1.0 g, 6.5 mmol) was added to a solution of 3-[3-(2-cyano-5-methylphenylsulfonyloxy)-5-methylphenoxy]-propanol (720 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 (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 (520 mg, 72%). 1H-NMR (300 MHz, CDCl3) δ 9.81 (s, 1H), 7.89 (s, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.55 (d, J=7.9 Hz, 1H), 6.62 (s, 1H), 6.60 (s, 1H), 6.56 (s, 1H), 4.22 (t, J=6.0 Hz, 2H), 2.85 (t, J=6.0 Hz, 2H), 2.49 (s, 3H), 2.25 (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-f38c0fdf1ce5449392c3a136158f9391
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

Loading…