4-Toluenesulfonyl chloride → [(2S)-oxolan-2-yl]methyl 4-methylbenzene-1-sulfonate

HRID 717230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717230
[O:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][OH:7].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:7][CH2:6][C@@H:2]2[CH2:3][CH2:4][CH2:5][O:1]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 637528(2S)-(+)-2-(Hydroxymethyl)tetrahydrofuran

Produkt 1

HCID 7033051[(2S)-oxolan-2-yl]methyl 4-methylbenzene-1-sulfonateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To (S)-(tetrahydrofuran-2-yl)methanol (2.0 g, 20 mmol) in CH2Cl2 (10 mL) at about 0° C. was added p-toluenesulfonyl chloride (4.2 g, 22.00 mmol), followed by drop-wise addition of triethylamine (5.6 mL, 40.0 mmol). The resulting solution was kept at 0° C. for 2 hours, and then at room temperature for another 2 hours. The reaction mixture was concentrated to dryness and diethylether (200 mL) and water (100 mL) were added. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated to yield the title compound (2.3 g, 13.00 mmol, 64%) as a colorless oil, which was used in the next step without purification.

Aufarbeitung

  1. waitat room temperature for another 2 hours
  2. concentrationThe reaction mixture was concentrated to dryness and diethylether (200 mL) and water (100 mL)
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cabacec7484a42a198bdd59132a64059
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193713B2

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