Water → 4-Hydroxy-4-(dimethylamino-ethyl)-3,5-dimethyl-2,5-heptadiene

HRID 1603179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1603179
Br[C:2](=[CH:4][CH3:5])[CH3:3].[Li].C(O[C:10](=[O:16])[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])C.O>C(OCC)C>[OH:16][C:10]([CH2:11][CH2:12][N:13]([CH3:14])[CH3:15])([C:2]([CH3:3])=[CH:4][CH3:5])[C:4]([CH3:5])=[CH:2][CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 209102-Bromobut-2-eneHCID 88372beta-Alanine, N,N-dimethyl-, ethyl esterHCID 3028194Lithium

Produkt 1

HCID 545060434-Hydroxy-4-(dimethylamino-ethyl)-3,5-dimethyl-2,5-heptadiene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2-bromo-2-butene (108 g; 0.800 mol) was added to 10.0 g of lithium (1.43 mol) in diethyl ether (300 ml) in about 30 minutes with reflux. After stirring overnight (17 hours), ethyl-3-(N,N-dimethylamino)propionate (52.0 g; 0.359 mol) was added to the reaction mixture in about 15 minutes. After stirring for 30 minutes at room temperature 200 ml of water was added dropwise. After separation the water phase was extracted two times with 50 ml of CH2Cl2. The organic phase was reduced by evaporation and the residue was distilled at reduced pressure. The yield was 51.0 g (67%).

Aufarbeitung

  1. temperaturewith reflux
  2. additionwas added to the reaction mixture in about 15 minutes
  3. additionwas added dropwise
  4. customAfter separation the water phase
  5. extractionwas extracted two times with 50 ml of CH2Cl2
  6. customThe organic phase was reduced by evaporation
  7. distillationthe residue was distilled at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d5a0a84cc3ec4bed810ffba6e19bbaf3
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05986029

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