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

HRID 452953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 452953
[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-ffb47826b40745edb85baa154c4a32d4
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492371B2

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