5-Cyano-2-furaldehyde → 5-(Hydroxymethyl)furan-2-carbonitrile

HRID 1654130

Reaction equation

HRID 1654130 reaction equation
[CH:1]([C:3]1[O:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=1)=[O:2].[BH4-].[K+].P([O-])(O)(O)=O.[Na+]>O1CCCC1.O>[OH:2][CH2:1][C:3]1[O:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6421395-Cyano-2-furaldehydeHCID 4192641Potassium borohydrideHCID 23672064Monosodium phosphate

Product 1

HCID 30214065-(Hydroxymethyl)furan-2-carbonitrileYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.87 g of the aldehyde of Stage A in 5 ml of tetrahydrofuran and 1 ml of water was cooled to 0° C. and 0.47 g of potassium borohydride were introduced. The mixture was stirred for 5 hours, poured into an aqueous sodium dihydrogenphosphate solution and extracted with isopropyl ether. The extract was dried and the solvent was evaporated to obtain 0.77 g of the expected product.

Workup

  1. extractionextracted with isopropyl ether
  2. customThe extract was dried
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5e604ca6abc64148b01f7f7b4b997bd6
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Linked notes

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