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

HRID 724893

Reaktionsgleichung

Reaktionsgleichung von HRID 724893
[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-04993b0fc7bd431ea10c6d6644caaf56
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05705487

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