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1-Butanol → 2-Butoxy-4-methylpyrimidine-5-carboxylic acid

HRID 917396
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 917396
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[OH-].[K+].CS([C:12]1[N:17]=[C:16]([CH3:18])[C:15]([C:19]([O:21]CC)=[O:20])=[CH:14][N:13]=1)(=O)=O>O>[CH2:1]([O:5][C:12]1[N:17]=[C:16]([CH3:18])[C:15]([C:19]([OH:21])=[O:20])=[CH:14][N:13]=1)[CH2:2][CH2:3][CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 2631-Butanol2×HCID 14797Potassium HydroxideHCID 23020175Ethyl 4-methyl-2-(methylsulfonyl)pyrimidine-5-carboxylate

Produkt 1

HCID 230201272-Butoxy-4-methylpyrimidine-5-carboxylic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 1.5 ml of butanol, 0.72 g (11 mmol) of 85.5% potassium hydroxide powder was suspended, followed by drop-wise adding, under ice-cooling, a 1.5 ml of butanol solution dissolving with 1.22 g (5.0 mmol) of ethyl 2-methansulfonyl-4-methylpyrimidine-5-carboxylate. After the end of the drop-wise addition, the solution was stirred at room temperature for 3 hours. To the reaction liquid, 50 ml of water was added, and the water layer was washed with diisopropyl ether, followed by adding 10% hydrochloric acid to make acidic, and extracting with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to obtain 0.87 g (yield: 83%) of 2-butoxy-4-methylpyrimidine-5-carboxylic acid.

Aufarbeitung

  1. additionadding, under ice-
  2. temperaturecooling
  3. additionAfter the end of the drop-wise addition
  4. additionwas added
  5. washthe water layer was washed with diisopropyl ether
  6. additionby adding 10% hydrochloric acid
  7. extractionextracting with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materiala saturated saline solution in this order, and dried over anhydrous magnesium sulfate
  10. concentrationThe solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-568b65bf71284c71b827e97deece46a9
Quelldatensatz
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07273878B2

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