Methyl4-(3-methylsulfinylphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate → Methyl 4-(3-mercaptophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

HRID 1108076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108076
[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17](C)=O)[CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[SH:17][C:13]1[CH:12]=[C:11]([C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH:16]=[CH:15][CH:14]=1

Komponenten

3

Edukt 1

HCID 11323524Methyl4-(3-methylsulfinylphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

Produkt 1

HCID 11242202Methyl 4-(3-mercaptophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9845Trifluoroacetic anhydrideLösungsmittel

Versuchsvorschrift

Methyl4-(3-methylsulfinylphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (12.2 g, 43 mmol) was dissolved in trifluoroacetic anhydride (50 ml) and heated at reflux for 30 min. Volatiles were removed by evaporation and the residue was dissolved into methyl alcohol (100 ml). Triethylamine (100 ml) was added over 5 min and the mixture concentrated to dryness. The residue was dissolved in ethyl acetate (500 ml), washed with saturated aqueous ammonium chloride (200 ml) and brine (200 ml), dried (magnesium sulfate) and concentrated to dryness to provide crude titled compound as a pale black liquid which was used as such without further purification.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 30 min
  3. customVolatiles were removed by evaporation
  4. dissolutionthe residue was dissolved into methyl alcohol (100 ml)
  5. additionTriethylamine (100 ml) was added over 5 min
  6. concentrationthe mixture concentrated to dryness
  7. dissolutionThe residue was dissolved in ethyl acetate (500 ml)
  8. washwashed with saturated aqueous ammonium chloride (200 ml) and brine (200 ml)
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-24163cfd1cf546998eb4f7cbafc5ea4e
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06063928

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