Acetone → (4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

HRID 1645639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645639
[CH2:1]([OH:7])[C@H:2]([OH:6])[CH2:3][CH2:4][OH:5].[CH3:8][C:9]([CH3:11])=O>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>[CH3:8][C:9]1([CH3:11])[O:6][C@H:2]([CH2:3][CH2:4][OH:5])[CH2:1][O:7]1

Komponenten

5

Edukt 2

HCID 180AcetoneHCID 69942791,2,4-Butanetriol, (2R)-

Produkt 1

HCID 11480522(4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolaneAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of (R)-(+)-1,2,4-butanetriol (30 g, 283 mmol), acetone (200 ml, 2724 mmol) and p-toluenesulfonic acid monohydrate (1.4 g, 7.36 mmol) was stirred at room temperature for 16.5 hours. To the reaction mixture, triethylamine was added and the mixture was concentrated. The crude product was purified by silica gel column chromatography (silica gel, elution solvent: heptane/ethyl acetate=1/0→1/1→1/3 gradient). Desired fractions were concentrated to obtain the title compound (29.9 g, 72.3% yield) as a colorless oil.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. customThe crude product was purified by silica gel column chromatography (silica gel, elution solvent: heptane/ethyl acetate=1/0→1/1→1/3 gradient)
  3. concentrationDesired fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-b0a2855e46c947d1849f7adbe5c3c262
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124780B2

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