4-Toluenesulfonyl chloride → HCID 59504841, Verbindung

HRID 1496939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1496939
[F:1][C:2]1([F:8])[CH2:5][CH:4]([CH2:6][OH:7])[CH2:3]1.C(N(CC)CC)C.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl.O>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:7][CH2:6][CH:4]2[CH2:5][C:2]([F:8])([F:1])[CH2:3]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Komponenten

7

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 45480377(3,3-Difluorocyclobutyl)methanol

Produkt 1

HCID 59504841HCID 59504841, VerbindungAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (3,3-difluorocyclobutyl)methanol (500 mg, 4.09 mmol, 1.00 equiv), triethylamine (662.6 mg, 6.55 mmol, 1.60 equiv), and 4-dimethylaminopyridine (750 mg, 6.14 mmol, 1.50 equiv) in CH2Cl2 (5 mL) under argon at 0° C. was added 4-methylbenzene-1-sulfonyl chloride (1.01 g, 5.30 mmol, 1.30 equiv) in portions. The resulting mixture was stirred overnight at ambient temperature. The mixture was then diluted with H2O (20 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified using flash column chromatography (silica gel, EtOAc/Hexanes (1:5)) to yield 1.1 g (97%) of a light yellow oil. 1H-NMR (300 MHz, CDCl3): δ ppm 7.77 (d, J=7.6 Hz, 2H), 7.34 (d, J=8.0 Hz, 2H), 4.03 (d, J=6.5 Hz, 2H), 2.75-2.50 (m, 2H), 2.50-2.36 (m, 4H), 2.36-2.08 (m, 2H).

Aufarbeitung

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-da659c9cb2d34c1b834fbb5cc3f97ffc
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199945B2

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