Ethyl vinyl ether → 2-Methyl-5-hydroxymethyl-5-nitro-1,3-dioxane

HRID 1111257

Reaktionsgleichung

Reaktionsgleichung von HRID 1111257
[OH:1][CH2:2][C:3]([CH2:9][OH:10])([CH2:7][OH:8])[N+:4]([O-:6])=[O:5].[CH2:11](OC=C)[CH3:12]>Cl.C(#N)C>[CH3:11][CH:12]1[O:8][CH2:7][C:3]([CH2:9][OH:10])([N+:4]([O-:6])=[O:5])[CH2:2][O:1]1

Komponenten

5

Edukt 2

HCID 8023Ethyl vinyl etherHCID 31337Tris(hydroxymethyl)nitromethane

Produkt 1

HCID 156709102-Methyl-5-hydroxymethyl-5-nitro-1,3-dioxaneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Following the procedure 2(A) described in this application, to a 100 ml round bottom flask equipped with a stir bar and reflux condenser topped with a nitrogen inlet was added 5 g (0.03 mol) tris(hydroxymethyl)nitromethane, 2.86 g (0.04 mol) ethylvinyl ether, 50 ml acetonitrile and 5 drops concentrated HCl. The reaction was heated to 35°-40° C. for 4 hours. After cooling to room temperature the volatiles were removed to give the product, 2-methyl-5-hydroxymethyl-5-nitro-1,3-dioxane, in 86% yield. 1H NMR in CD3OD confirmed the structure.

Aufarbeitung

  1. customdescribed in this application, to a 100 ml round bottom flask
  2. customequipped with a stir bar
  3. temperaturereflux condenser
  4. customtopped with a nitrogen inlet
  5. temperatureThe reaction was heated to 35°-40° C. for 4 hours
  6. customwere removed

Quellen und Nachweise

ORD-Eintrag
ord-8261094aa39048659cc3d9f4fdbfe303
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04978793

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