4-Toluenesulfonyl chloride → (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 78495

Reaktionsgleichung

Reaktionsgleichung von HRID 78495
[CH2:1]([OH:7])[C@@H:2]1[O:6][CH2:5][CH2:4][CH2:3]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:7][CH2:1][C@H:2]2[CH2:3][CH2:4][CH2:5][O:6]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 6931745(2R)-oxolan-2-ylmethanol

Produkt 1

HCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-tetrahydrofurfuryl alcohol (Lancaster, 1.0 g, 9.8 mmol) in 5 mL of CH2Cl2 and 5 mL of pyridine was added p-toluenesulfonyl chloride (2.8 g, 14.7 mmol) in portions over 15 minutes. The mixture was stirred at ambient temperature for 3 hours and was quenched with 5 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with three 5 mL of portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound. MS (DCI/NH3) m/z 257 (M+H)+, 274 (M+NH4)+.

Aufarbeitung

  1. customwas quenched with 5 mL of saturated, aqueous NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with three 5 mL of portions of CH2Cl2
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6112f70ce11f4bf3ba40866143eaf924
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841334B2

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