4-Toluenesulfonyl chloride → (2,2-Dimethyl-1,3-dioxan-5-yl)methyl 4-methylbenzenesulfonate

HRID 45266

Reaktionsgleichung

Reaktionsgleichung von HRID 45266
[CH3:1][C:2]1([CH3:10])[O:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][O:3]1.CCN(CC)CC.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([O:9][CH2:8][CH:5]2[CH2:6][O:7][C:2]([CH3:10])([CH3:1])[O:3][CH2:4]2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanol

Produkt 1

HCID 14893699(2,2-Dimethyl-1,3-dioxan-5-yl)methyl 4-methylbenzenesulfonateAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1.5 g (10.26 mmol) of (2,2-dimethyl-1,3-dioxan-5-yl)methanol and 1.71 mL of Et3N in 15 mL of DCM, cooled to 0° C., are added 2.15 g (11.3 mmol) of tosyl chloride. The medium is allowed to warm to room temperature, and stirring is continued for 1 hour. The medium is taken up in 100 mL of DCM, washed successively with 0.11N HCl (2×20 mL) and brine (20 mL), dried over Na2SO4, concentrated under reduced pressure and then purified by chromatography on a column of silica gel, eluting with a 99/1 DCM/MeOH mixture. 3 g of (2,2-dimethyl-1,3-dioxan-5-yl)methyl 4-methylbenzenesulfonate are obtained in the form of a colourless oil.

Aufarbeitung

  1. washwashed successively with 0.11N HCl (2×20 mL) and brine (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. custompurified by chromatography on a column of silica gel
  5. washeluting with a 99/1 DCM/MeOH mixture

Quellen und Nachweise

ORD-Eintrag
ord-071deeeea2fb4163a8d68979ab244abc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541455B2

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