2-Butyn-1-ol → HCID 22599675, Verbindung

HRID 1592167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1592167
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])[N:12]=[CH:11][N:10]=1)[C:4]#[C:5][CH3:6]

Komponenten

6

Edukt 4

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 225996714-Chloro-6-(2-chloro-6-fluorobenzyl)pyrimidine

Produkt 1

HCID 22599675HCID 22599675, VerbindungAusbeute 115 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

In 2 ml of tetrahydrofuran was suspended 0.05 g of sodium hydride (60% in oil), to which 0.6 ml of a tetrahydrofuran solution containing 0.07 g of 2-butyn-1-ol was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 20 minutes, to which 0.6 ml of a tetrahydrofuran solution containing 0.2 g of 4-chloro-6-(2-chloro-6-fluorobenzyl)pyrimidine was slowly added dropwise at room temperature, followed by stirring for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.26 g of 4-(2-butynyloxy)-6-(2-chloro-6-fluorobenzyl)pyrimidine (the present compound (101)).

Aufarbeitung

  1. additionwas slowly added dropwise
  2. additionwas slowly added dropwise at room temperature
  3. stirringby stirring for 4 hours
  4. extractionextracted three times with chloroform
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-778ecdc5fd7d4a52beb7514e86adf3e8
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291730B2

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