Thionyl Chloride → 5,6-Dihydro-5,5-dimethyl-4H-1,3,2-dioxathiin 2-oxide

Reaktionsgleichung

[S:1](Cl)(Cl)=[O:2].[CH3:5][C:6]([CH3:11])([CH2:9][OH:10])[CH2:7][OH:8]>ClCCl>[CH3:5][C:6]1([CH3:11])[CH2:9][O:10][S:1](=[O:2])[O:8][CH2:7]1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

Thionylchloride (735 mL) is added to a solution of 2,2-dimethylpropane-1,3-diol (1 g) in dichloromethane (10 mL) chilled in an ice bath. The mixture is heated to 40° C. for 3 hours and partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The organic phase is washed with brine, dried (MgSO4) and concentrated to give the title compound. Yield: 535 mg; TLC: rf=0.65 (silicagel, cyclohexane/ethyl acetate 3:1).

Aufarbeitung

temperaturechilled in an ice bath
custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane
washThe organic phase is washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-af424466045b46e7854c08638e34faf0
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08642585B2

Notizen zur Reaktion

Wird geladen…

Komponenten

Edukt 2

HCID 24386Thionyl Chloride

HCID 31344Neopentyl glycol

Produkt 1

HCID 108772945,6-Dihydro-5,5-dimethyl-4H-1,3,2-dioxathiin 2-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel