Dimethyl Sulfoxide → HCID 54390465, compound

HRID 442932Notes

Reaction equation

HRID 442932 reaction equation
[CH3:1][O:2][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].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[CH3:1][O:2][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]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 54075637HCID 54075637, compound

Product 1

HCID 54390465HCID 54390465, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 528 mg (1.44 mmol) of 3-[3-(2-methoxy-5-methylphenylsulfonyloxy)-5-methylphenoxy]propanol, as prepared in the preceding step, 527 μL (3.02 mmol) of N,N-diisopropylethylamine and 307 μL (4.32 mmol) of anhydrous dimethyl sulfoxide in 6.0 mL of anhydrous dichloromethane was added 459 mg (2.88 mmol) of sulfur trioxide pyridine complex. The mixture was warmed to ambient temperature over 30 min and stirred for 16 h. The mixture was poured into 15 mL of dichloromethane and washed with 5% (w/v) aqueous citric acid (2×25 mL). Each wash was extracted with 5 mL of dichloromethane and the combined extracts were washed with brine (25 mL), dried over Na2SO4 and concentrated. The resulting material was chromatographed on 35 g of silica gel with dichloromethane followed by 3% ethyl acetate-dichlorometharie to afford 320 mg (61%) of the title compound as a colorless syrup: 1H-NMR (300 MHz; CDCl3) δ 9.83 (t, 1 H, J=1.4 Hz), 7.63 (d, 1 H, J=2.3 Hz), 7.40 (dd, 1 H, J=8.5, 2.3 Hz), 6.98 (d, 1 H, J=8.5 Hz), 6.59 (br s, 1 H), 6.55 (br s, 1 H), 6.46 (t, 1 H, J=2.1 Hz), 4.19 (t, 2 H, J=6.1 Hz), 3.98 (s, 3 H), 2.85 (td, 2 H, J=6.1, 1.4 Hz), 2.29 (s, 3 H) and 2.25 (s, 3 H).

Workup

  1. additionwas added 459 mg (2.88 mmol) of sulfur trioxide pyridine complex
  2. temperatureThe mixture was warmed to ambient temperature over 30 min
  3. washwashed with 5% (w/v) aqueous citric acid (2×25 mL)
  4. extractionEach wash was extracted with 5 mL of dichloromethane
  5. washthe combined extracts were washed with brine (25 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe resulting material was chromatographed on 35 g of silica gel with dichloromethane

Sources & evidence

ORD record
ord-e759859e35be4ccba2c9560ae879a592
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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