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Benzenesulfonyl chloride → HCID 21387469, Verbindung

HRID 1834342
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1834342
[O:1]=[C:2]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[CH2:3][P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6].[H-].[Na+].C([Li])CCC.C1(S([Cl:38])(=O)=O)C=CC=CC=1>CCCCCC.C(O)(=O)C.O1CCCC1>[O:1]=[C:2]([CH:10]([Cl:38])[CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[CH2:3][P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 357799HCID 357799, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 21387469HCID 21387469, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic Acid
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel3×
HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under an atmosphere of nitrogen, a solution of 4.2 g. of dimethyl 2-oxo-7-(2-tetrahydropyranyloxy)-heptylphosphonate (prepared as described above) in 15 ml. of tetrahydrofuran was added to a suspension of 596 mg. of sodium hydride (63% content) in 20 ml. of tetrahydrofuran at room temperature, and the mixture was stirred at the same temperature for 30 minutes. After cooling to 0° C., 14 ml. of a 1.3M solution of n-butyllithium in n-hexane were added to the solution and the mixture was stirred at 0° C. for 30 minutes. After cooling the solution to -78° C., there was added a solution of 3.23 g. of benzenesulphonyl chloride in 10 ml. of tetrahydrofuran. The mixture was stirred at -78° C. for one hour and then at room temperature for one hour. The reaction mixture was acidified to pH 3 with acetic acid and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and benzene (5:1) as eluent to give 2.97 g. of the title compound having the following physical characteristics:-

Aufarbeitung

  1. temperatureAfter cooling the solution to -78° C.
  2. additionthere was added a solution of 3.23 g
  3. stirringThe mixture was stirred at -78° C. for one hour
  4. waitat room temperature for one hour
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel using
  11. additiona mixture of ethyl acetate and benzene (5:1) as eluent
  12. customto give 2.97 g

Quellen und Nachweise

ORD-Eintrag
ord-6a87308bfd5c43458e8d3d49a6890eda
Quelldatensatz
uspto-grants-1978_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04069387

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