tert-Butanol → Tert-butyl hex-5-enoate

HRID 1675996

Reaktionsgleichung

Reaktionsgleichung von HRID 1675996
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[C:9](O)([CH3:12])([CH3:11])[CH3:10]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Komponenten

5

Edukt 2

HCID 6386tert-ButanolHCID 153085-Hexenoic Acid

Produkt 1

HCID 15047738Tert-butyl hex-5-enoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-hexenoic acid (15.2 mL, 0.131 mol) in DCM (375 mL), cooled to 0° C., tert-butanol (176 mL, 1.84 mol) and then 4-dimethylaminopyridine (3.21 g, 26.3 mmol) were added. The mixture was stirred at room temperature for 22 hrs, filtered and concentrated. The residue was redissolved in DCM/n-hexane and concentrated under reduced pressure. The crude oil was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 5 to 10%), affording the title product.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in DCM/n-hexane
  4. concentrationconcentrated under reduced pressure
  5. customThe crude oil was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 5 to 10%)

Quellen und Nachweise

ORD-Eintrag
ord-4a6c1114470a47deadac8d43de1917a9
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003811B2

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