4-Toluenesulfonyl chloride → 3-Fluoroprop-1-yl toluene-4-sulphonate

HRID 1426999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426999
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[F:19][CH2:20][CH2:21][CH2:22][OH:23].O1CCCC1>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.O>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:23][CH2:22][CH2:21][CH2:20][F:19])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Komponenten

8

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 680423-Fluoro-1-propanol

Produkt 1

HCID 63667743-Fluoroprop-1-yl toluene-4-sulphonateAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Triethylamine (11 mL, 79.4 mmol), 4-dimethylaminopyridine (390 mg, 3.19 mmol), and p-toluenesulfonyl chloride (13.4 g, 70.4 mmol) were added to a mixture of commercially available 3-fluoropropan-1-ol (5.0 g, 64 mmol) and tetrahydrofuran (120 mL) under nitrogen atmosphere at 0° C., and the mixture was stirred at mom temperature for 90 hours. Water and ethyl acetate were added to the reaction mixture for partition. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated, the resultant residue was dissolved in dichloromethane and n-heptane, and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=10:1-2:1) to obtain the title compound (12.7 g, 85%).

Aufarbeitung

  1. customfor partition
  2. washThe organic layer was washed with water
  3. dry with materiala saturated saline solution, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. dissolutionthe resultant residue was dissolved in dichloromethane
  7. customn-heptane, and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=10:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-8ccc62cf18914ea49310ce1f325ecf82
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933099B2

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