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Ethyl 2-hydroxyisobutyrate → Ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoate

HRID 2047474
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2047474
[OH:1][C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:10](Cl)(=[O:21])[O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>C(#N)C.CN(C1C=CN=CC=1)C.O>[CH3:8][C:2]([O:1][C:10]([O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1)=[O:21])([CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 6653Ethyl 2-hydroxyisobutyrateHCID 821294-Nitrophenyl chloroformate

Produkt 1

HCID 67232782Ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel
HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-hydroxy-2-methylpropanoate (1.2 g) and 4-nitrophenyl chlorocarbonate (1.2 g) in acetonitrile (20 mL) was added DMAP (0.77 g) at 0° C., and the mixture was stirred at room temperature for 3 days. The mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 0→25% ethyl acetate/hexane) to give ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoate (1.3 g, 74%) as a pale-yellow oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (solvent gradient; 0→25% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ffc2398177eb47e5a9845913ce9b6bb4
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08592454B2

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