Ethanol → (5-[1,3]Dioxolan-2-yl-pyridin-2-yl)-methanol

HRID 640439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 640439
C(O)C.O1CCCC1.[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[C:14]1[CH:15]=[CH:16][C:17]([CH:20]=[O:21])=[N:18][CH:19]=1.[BH4-].[Na+]>O>[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][OH:21])=[N:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 592551735-(1,3-Dioxolan-2-yl)picolinaldehyde

Produkt 1

HCID 59255267(5-[1,3]Dioxolan-2-yl-pyridin-2-yl)-methanolAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To an ethanol (20 mL) and tetrahydrofuran (20 mL) solution of 5-[1,3]dioxolan-2-yl-pyridine-2-carbaldehyde (1.73 g, 9.66 mmol) described in Manufacturing Example 154-1-3 was added sodium borohydride (731 mg, 19.3 mmol), which was stirred for 25 minutes at room temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:2) to obtain the title compound (1.37 g, 78%).

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-d266718a90e54b27b5a44492e4448e40
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691882B2

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