4-Toluenesulfonyl chloride → HCID 86732633, Verbindung

HRID 626392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626392
[O:1]1[CH2:4][CH2:3][C@@H:2]1[CH2:5][CH2:6][OH:7].[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:15][C:14]1[CH:16]=[CH:17][C:11]([S:8]([O:7][CH2:6][CH2:5][C@H:2]2[CH2:3][CH2:4][O:1]2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 89304729HCID 89304729, Verbindung

Produkt 1

HCID 86732633HCID 86732633, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The mixture of (S)-2-(oxetan-2-yl)ethanol (408 mg, 4 mmol), TsCl (1.15 g, 6 mmol), TEA (0.85 g, 6 mmol) and DMAP (92 mg, 0.8 mmol) in DCM (20 mL) was stirred at RT for 18 h. Then the mixture was concentrated, the residue was dissolved into EtOAc (15 mL), washed with sat. NaHCO3 aqueous solution, water and brine, then the EtOAc layers was dried with Na2SO4, then the solvent was removed under the reduced pressure. The crude product was purified with Combiflash (PE/EtOAc=5/1, silica gel) to give the titled compound.

Aufarbeitung

  1. concentrationThen the mixture was concentrated
  2. dissolutionthe residue was dissolved into EtOAc (15 mL)
  3. washwashed with sat. NaHCO3 aqueous solution, water and brine
  4. dry with materialthe EtOAc layers was dried with Na2SO4
  5. customthe solvent was removed under the reduced pressure
  6. customThe crude product was purified with Combiflash (PE/EtOAc=5/1, silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-3fc4b1bbecee437bafd54cb3c481c398
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309227B2

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