Dimethyl Sulfoxide → HCID 53901878, compound

HRID 442975Notes

Reaction equation

HRID 442975 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([O:11][C:12]2[CH:13]=[C:14]([CH:20]=[C:21]([CH3:23])[CH:22]=2)[O:15][CH2:16][CH2:17][CH2:18][OH:19])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([S:8]([O:11][C:12]2[CH:13]=[C:14]([CH:20]=[C:21]([CH3:23])[CH:22]=2)[O:15][CH2:16][CH2:17][CH:18]=[O:19])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 53853402HCID 53853402, compound

Product 1

HCID 53901878HCID 53901878, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-[3-(3-fluorophenylsulfonyloxy)-5-methylphenoxy]-propanol (840 mg, 2.5 mmol, as prepared in the preceding step), N,N-diisopropylethylamine (0.90 mL, 25.2 mmol), anhydrous dimethyl sulfoxide (0.52 mL, 27.4 mmol), and anhydrous dichloromethane (25.9 mL) was cooled to 0° C. under nitrogen. Sulfur trioxide pyridine complex (830 mg, 5.2 mmol) was added in portions over 13 minutes. The solution was stirred at 0° C. for 2.75 hours, then the reaction was quenched with 10% aqueous citric acid (60 mL). Diethyl ether (60 mL) was added, and the mixture was extracted. The aqueous layer was extracted with diethyl ether (30 mL), and the combined organic layers were washed with 5% aqueous citric acid (100 mL). The aqueous layer was extracted with diethyl ether (30 mL), and the combined organic layers were washed with pH 7 buffer (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to an oil. The crude product was purified by flash column chromatography through silica gel (40% diethyl ether in hexane) to give the title compound as a pale yellow oil (468 mg, 56%). 1H-NMR (300 MHz, CDCl3) δ 9.84 (t, 1H, J=1.4 Hz), 7.51-7.68 (m, 3H), 7.35-7.42 (m, 1H), 6.63 (br s, 1H), 6.44 (br s, 1H), 6.37 (br t, 1H, J=2.2 Hz), 4.20 (t, 2H, J=6.1 Hz), 2.87 (td, 2H, J=1.4, 6.1 Hz), 2.26 (s, 3H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C16H15FO5S: 361.1 (M+Na). Found: 361.3.

Workup

  1. additionSulfur trioxide pyridine complex (830 mg, 5.2 mmol) was added in portions over 13 minutes
  2. customthe reaction was quenched with 10% aqueous citric acid (60 mL)
  3. additionDiethyl ether (60 mL) was added
  4. extractionthe mixture was extracted
  5. extractionThe aqueous layer was extracted with diethyl ether (30 mL)
  6. washthe combined organic layers were washed with 5% aqueous citric acid (100 mL)
  7. extractionThe aqueous layer was extracted with diethyl ether (30 mL)
  8. washthe combined organic layers were washed with pH 7 buffer (50 mL) and brine (50 mL)
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated to an oil
  12. customThe crude product was purified by flash column chromatography through silica gel (40% diethyl ether in hexane)

Sources & evidence

ORD record
ord-0f287118477f4f5284bfdc9080d4a8e5
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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