Ammonium Chloride → 5-(Hydroxymethyl)furan-2-carbonitrile

HRID 1585890

Reaction equation

HRID 1585890 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([C:10]#[N:11])=[CH:8][CH:9]=1)=O.[BH4-].[Na+].[NH4+].[Cl-]>C(O)C>[OH:2][CH2:3][C:5]1[O:6][C:7]([C:10]#[N:11])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 13011707Methyl 5-cyanofuran-2-carboxylate

Product 1

HCID 30214065-(Hydroxymethyl)furan-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the ester from step 1 (0.098 g, 0.652 mmol), in ethanol (2.5 ml) at 0° C. was treated with sodium borohydride (0.11 g, 2.936 mmol) and the reaction was stirred for 2 hrs. Saturated NH4Cl solution (1 ml) was added and the aqueous extracted with diethylether. The combined extracts were dried (MgSO4) and evaporated in vacuo. The residue was chromatographed (silica gel, diethylether) to afford the title compound.

Workup

  1. extractionthe aqueous extracted with diethylether
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue was chromatographed (silica gel, diethylether)

Sources & evidence

ORD record
ord-92585bef1193432a95ed990f1dd1fe62
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Linked notes

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