Dimethyl Sulfoxide → 3-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propionaldehyde

HRID 442929

Reaktionsgleichung

Reaktionsgleichung von HRID 442929
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH2:19][OH:20])(=[O:11])=[O:10])#[N:2].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH:19]=[O:20])(=[O:11])=[O:10])#[N:2]

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 186697063-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol

Produkt 1

HCID 227224093-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propionaldehydeAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sulfur trioxide pyridine complex (480 mg, 3.0 mmol) was added to a solution of 3-[3-(2-cyanophenylsulfonyloxy)-5-methylphenoxy]propanol (315 mg, 0.9 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.5 mL, 3.9 mmol) and anhydrous dimethyl sulfoxide (0.2 mL, 2.8 mmol) in anhydrous dichloromethane (10 mL). The reaction mixture was stirred at ambient temperature for 1 hour and then quenched with 10% aqueous citric acid (30 mL). The mixture was extracted into dichloromethane (3×40 mL), and the dichloromethane solution was washed with 10% aqueous citric acid (30 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 (260 mg, 83%). 1H-NMR (300 MHz, CDCl3) δ 9.84 (s, 1H), 8.11 (m, 1H), 7.94 (m, 1H), 7.78-7.81 (m, 2H), 6.65 (s, 1H), 6.61 (s, 1H), 6.57 (s, 1H), 4.24 (t, J=6.0 Hz, 2H), 2.88 (t, J=6.0 Hz, 2H), 2.27 (s, 3H).

Aufarbeitung

  1. customquenched with 10% aqueous citric acid (30 mL)
  2. extractionThe mixture was extracted into dichloromethane (3×40 mL)
  3. washthe dichloromethane solution was washed with 10% aqueous citric acid (30 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent in vacuo
  6. customthe residue was purified by flash column chromatography (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-b75a38a8c82c488299e6b949eded41fc
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891909

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