Neopentyl alcohol → 2,2-Dimethylpropyl trifluoromethanesulfonate

HRID 20411

Reaktionsgleichung

Reaktionsgleichung von HRID 20411
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH2:16](O)[C:17]([CH3:20])([CH3:19])[CH3:18].N1C(C)=CC=CC=1C>ClCCl>[CH3:16][C:17]([CH3:20])([CH3:19])[CH2:18][O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4]

Komponenten

5

Edukt 3

HCID 6404Neopentyl alcoholHCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydride

Produkt 1

HCID 156962812,2-Dimethylpropyl trifluoromethanesulfonateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add trifluoromethanesulphonic anhydride (1.12 mL, 6.8 mmol) to a solution of neopentylalcohol (0.5 g, 5.7 mmol) and 2,6-lutidine (0.7 mL, 6.8 mmol) in dichloromethane (10 mL) at −78° C. and stir for 1 hour. Add water to quench the reaction, separate the organic layer and extract the aqueous layer with dichloromethane. Combine the organic layers, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 1:4 hexane:dichloromethane) to give the desired compound as an oil (0.9 g, 72% yield).

Aufarbeitung

  1. customAdd water to quench
  2. customthe reaction
  3. customseparate the organic layer
  4. extractionextract the aqueous layer with dichloromethane
  5. dry with materialdry (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 1:4 hexane:dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-6975154842644f7fbddb9e327f2bcaee
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745438B2

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