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Lithium Hydroxide → 2-(6-Bromo-pyridin-2-yl)-3-methoxymethoxy-2-methoxymethoxymethyl-propionic acid

HRID 474044
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 474044
[OH-].[Li+].C([O:5][C:6](=[O:25])[C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=1)([CH2:13][O:14][CH2:15][O:16][CH3:17])[CH2:8][O:9][CH2:10][O:11][CH3:12])C>C(O)C.O>[Br:24][C:20]1[N:19]=[C:18]([C:7]([CH2:8][O:9][CH2:10][O:11][CH3:12])([CH2:13][O:14][CH2:15][O:16][CH3:17])[C:6]([OH:25])=[O:5])[CH:23]=[CH:22][CH:21]=1
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Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 866680172-(6-Bromo-pyridin-2-yl)-3-methoxymethoxy-2-methoxymethoxymethyl-propionic acid ethyl ester

Produkt 1

HCID 866680182-(6-Bromo-pyridin-2-yl)-3-methoxymethoxy-2-methoxymethoxymethyl-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Lithium hydroxide (10.69 g, 254.95 mmol) was added to a solution of 2-(6-bromo-pyridin-2-yl)-3-methoxymethoxy-2-methoxymethoxymethyl-propionic acid ethyl ester (20.0 g, 50.99 mmol) in ethanol (100 ml) and water (100 ml) at rt and the reaction mixture was allowed to stir overnight. The reaction mass was concentrated under reduced pressure and acidified with dilute HCl and at 0° C. The product was extracted with ethyl acetate, washed with minimum amount of brine. Organic layer was concentrated under reduced pressure to obtain title compound as a brown liquid. Yield=18.0 g. TLC (50% ethyl acetate in hexane) Rf=0.05; LCMS: RtH9=1.383, [M+1]=364.0 and 366.0; HPLC: RtH9=3.844 min (49%) and 3.885 min. (22%).

Aufarbeitung

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. customacidified with dilute HCl and at 0° C
  3. extractionThe product was extracted with ethyl acetate
  4. washwashed with minimum amount of brine
  5. concentrationOrganic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-38f7e4410ded4b9f93d0b495336ef199
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08637508B2

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