4-Toluenesulfonyl chloride → 2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

HRID 85118

Reaktionsgleichung

Reaktionsgleichung von HRID 85118
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.C(N(CC)CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:8][CH2:7][CH:5]2[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 7528SolketalHCID 8471Triethylamine

Produkt 1

HCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(2,2-Dimethyl-1,3-dioxolan-4-yl)methanol (33; 7.56 mmol, 1.0 g) was taken up in 20 mL of dichloromethane. Triethylamine (26.46 mmol, 3.687 mL) was then added, followed by p-toluensulfonyl chloride (15.12 mmol, 2.88 g) and catalytic amount of 4-dimethylamino pyridine. The reaction was allowed to stir at room temperature for 18 h. The crude reaction mixture was diluted with dichloromethane, washed successively with saturated aqueous sodium bicarbonate solution, water, dried (Na2SO4) and concentrated under reduced pressure. The resulting residue 34 was used for the next step without further purification (89% crude yield).

Aufarbeitung

  1. customThe crude reaction mixture
  2. washwashed successively with saturated aqueous sodium bicarbonate solution, water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue 34 was used for the next step without further purification (89% crude yield)

Quellen und Nachweise

ORD-Eintrag
ord-ac5e6c1e7fdd4b0881b08a7d39fef9a6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

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