Sodium borohydride → 5-(Hydroxymethyl)thiophene-2-carbonitrile

HRID 1596

Reaktionsgleichung

Reaktionsgleichung von HRID 1596
[C:1]([C:3]1[S:4][C:5]([CH:8]=[O:9])=[CH:6][CH:7]=1)#[N:2].[BH4-].[Na+]>CCO>[C:1]([C:3]1[S:4][C:5]([CH2:8][OH:9])=[CH:6][CH:7]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 122800045-Formylthiophene-2-Carbonitrile

Produkt 1

HCID 106068135-(Hydroxymethyl)thiophene-2-carbonitrileAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-cyano-5-formyl-thiophene (6.9 g, 50 mmol) in EtOH (100 mL) was added sodium borohydride (1.9 g, 50 mmol) in portions. After 5 min of stirring, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and brine. The layers were separated and the organic phase was washed once with 1M citric acid and once with brine, then dried (MgSO4), filtered and concentrated in vacuo to give 6.1 g (88%) of 2-cyano-5-(hydroxymethyl)thiophene.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and brine
  3. customThe layers were separated
  4. washthe organic phase was washed once with 1M citric acid and once with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a1b67cc5004d4967b21c8097f4c0e66d
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726159

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