Triethylamine → Ethyl (2-propyl-1,3-dioxan-2-yl)acetate

HRID 1645539

Reaktionsgleichung

Reaktionsgleichung von HRID 1645539
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:12](O)[CH2:13][CH2:14][OH:15].C(OC)(OC)OC.C(N(CC)CC)C>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:9]([C:2]1([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[O:15][CH2:14][CH2:13][CH2:12][O:1]1)[CH2:10][CH3:11]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 9005Trimethyl orthoformateHCID 104421,3-PropanediolHCID 238498Ethyl 3-oxohexanoate

Produkt 1

HCID 59792385Ethyl (2-propyl-1,3-dioxan-2-yl)acetateAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 521998p-Toluenesulfonic acid monohydrateKatalysator

Versuchsvorschrift

A mixture of ethyl 3-oxohexanoate (5 g, 31.6 mmol), 1,3-propanediol (3.61 g, 47.4 mmol), trimethyl orthoformate (5.78 ml, 34.8 mmol), and p-toluenesulfonic acid monohydrate (272 mg, 1.58 mmol) was stirred at room temperature for 22 hours. After completion of the reaction, triethylamine (881 μl, 6.32 mmol) was added to the reaction mixture which was then concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (5.5 g, yield: 80.5%) as a light yellow oil.

Aufarbeitung

  1. additionwas added to the reaction mixture which
  2. concentrationwas then concentrated
  3. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d7dfc88dd4f2486aa12d1969aa2027c1
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124780B2

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