Methanol → 4-(Hydroxymethyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 1186428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186428
[C:1]([C:3]1([C:9](OC)=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].CO.O.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:1]([C:3]1([CH2:9][OH:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 962Water2×HCID 4311764Sodium borohydrideHCID 16726727Methyl 4-cyanooxane-4-carboxylate

Produkt 1

HCID 249369984-(Hydroxymethyl)tetrahydro-2H-pyran-4-carbonitrileAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (2.93 g, 17.3 mmol) was dissolved in tetrahydrofuran (50 mL), methanol (10 mL) and water (5.0 mL). To this, sodium borohydride (1.31 g, 34.6 mmol) was added and the mixture was stirred at room temperature for 30 minutes. The reaction was stopped by addition of water to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to give 4-cyanotetrahydro-2H-pyran-4-ylmethanol (1.59 g, yield: 92%).

Aufarbeitung

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e0a4dcaf845e4ea990aabfca7bdeca90
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673908B2

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