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Hexylene Glycol → 1-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-cyclopropanecarboxylic acid ethyl ester

HRID 512132
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 512132
[CH2:1]([O:3][C:4]([C:6]1([C:9]#[N:10])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:11][C:12](O)([CH2:14][CH:15]([OH:17])[CH3:16])[CH3:13]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[O:17][CH:15]([CH3:16])[CH2:14][C:12]([CH3:13])([CH3:11])[N:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 7870Hexylene GlycolHCID 380810Ethyl 1-cyanocyclopropanecarboxylate

Produkt 1

HCID 151932001-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-cyclopropanecarboxylic acid ethyl esterAusbeute 61.730,301 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To concentrated sulfuric acid (102 mL) was added 1-cyano-cyclopropanecarboxylic acid ethyl ester (60 g, 0.43 mol) dropwise followed by 2-methylpentan-2,4-diol (52 g, 0.44 mmol) dropwise at 0° C. The mixture was stirred for an additional 1 h at 0° C. then poured onto ice-water. The aqueous phase was washed with AcOEt (3×200 mL) and then basified to pH 12 with 10 M NaOH. The resulting mixture was extracted with EtOAc (3×500 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel to give 1-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-cyclopropanecarboxylic acid ethyl ester (65 g, yield: 63.2%). 1H NMR (CDCl3 400 MHz): δ4.21-4.06 (m, 3H), 1.73-1.69 (m, 1H), 1.40-1.10 (m, 17H).

Aufarbeitung

  1. additionthen poured onto ice-water
  2. washThe aqueous phase was washed with AcOEt (3×200 mL)
  3. extractionThe resulting mixture was extracted with EtOAc (3×500 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-70ce7543b46a475e9dd886e37ebb2344
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09102591B2

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