Triethylamine → 6-(Hydroxymethyl)pyridine-2-carbonitrile
Reaktionsgleichung
[C:1]([C:3]1[CH:11]=[CH:10][C:6](C(O)=O)=[CH:5][N:4]=1)#[N:2].CCN(CC)CC.Cl[C:20](OCC)=[O:21].[BH4-].[Na+]>C1COCC1>[OH:21][CH2:20][C:5]1[N:4]=[C:3]([C:1]#[N:2])[CH:11]=[CH:10][CH:6]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 6-cyanonicotinic acid (12 g, 0.081 mol; see step (i) above) in THF at 0° C., Et3N (12.4 mL, 0.0892 mol) was added followed by ethyl chloroformate (8.53 mL, 0.0892 mol). The reaction mixture was stirred for 15 min and NaBH4 (6.14 g, 0.162 mol) was added. Then the mixture was stirred at RT overnight, quenched with water and extracted with methylene chloride. The organic layer was concentrated and purified by column chromatography to yield 4 g (20%) of the alcohol.
Aufarbeitung
- stirringThen the mixture was stirred at RT overnight
- customquenched with water
- extractionextracted with methylene chloride
- concentrationThe organic layer was concentrated
- custompurified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-0241f58821ee42dc91fe93b06ca869c6
- Quelldatensatz
- uspto-grants-2006_10
- Patentnummer
- US07129233B2
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