Triethylamine → 2-((Benzyloxy)methyl)-1,3-dioxane

HRID 31641

Reaktionsgleichung

Reaktionsgleichung von HRID 31641
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12](O)[CH2:13][CH2:14][OH:15].C(OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>>[CH2:1]([O:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 5

HCID 8471TriethylamineHCID 104421,3-PropanediolHCID 31214Ethyl orthoformateHCID 108989(Phenylmethoxy)acetaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 597923782-((Benzyloxy)methyl)-1,3-dioxaneAusbeute 58 %

Versuchsvorschrift

A mixture of benzyloxyacetaldehyde (3.6 g, 24 mmol), 1,3-propanediol (5.2 ml, 72 mmol), triethyl orthoformate (4 ml, 24 mmol), and p-toluenesulfonic acid monohydrate (414 mg, 2.45 mmol) was stirred at room temperature for 17 hours. To the reaction mixture, triethylamine (669 μl, 4.8 mmol) was added, which was concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (2.9 g, yield: 58%) as a light yellow oil.

Aufarbeitung

  1. concentrationwhich was concentrated
  2. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9f39e15806ee44feb5cf00cee9492e0e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

Verknüpfte Notizen

Wird geladen…