1-(2-Chloropyrimidin-5-yl)ethan-1-one → 2-(2-Chloropyrimidin-5-yl)propan-2-ol

HRID 1046098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1046098
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][N:3]=1.[CH3:11][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])([CH3:11])[CH3:9])=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 137157421-(2-Chloropyrimidin-5-yl)ethan-1-oneHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 137157472-(2-Chloropyrimidin-5-yl)propan-2-olAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 1-(2-chloropyrimidin-5-yl)ethanone (268 mg, 1.7 mmol) in THF (20 mL) was added MeMgBr (2.68 mL, 8.04 mmol) at −78° C. under nitrogen. The solution was stirred at −78° C. for 20 min, quenched with satd aq NH4Cl, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give an oil, which was purified by prep TLC (PE:EA 3:1) to give 2-(2-chloropyrimidin-5-yl)propan-2-ol (150 mg, yield 51%).

Aufarbeitung

  1. customquenched with satd aq NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto give an oil, which
  6. customwas purified by prep TLC (PE:EA 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-1e03a37a646048bb874be26cc8541abf
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569292B2

Notizen zur Reaktion

Wird geladen…