2-Thiophenecarboxaldehyde → Thien-2-yl-hydroxyacetonitrile

HRID 485615

Reaction equation

HRID 485615 reaction equation
[CH:1]([C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)=[O:2].[C-:8]#[N:9].[Na+].[O-]S([O-])=O.[Na+]>O>[S:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[CH:1]([OH:2])[C:8]#[N:9]

Participants

5

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 8929Sodium CyanideHCID 6399220CID 63992202×

Product 1

HCID 11469116Thien-2-yl-hydroxyacetonitrileYield 59.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In this example 25.0 g of 2-formylthiophene was added to a stirred solution containing 10.93 g of sodium cyanide in 37 ml of water at room temperature. 63 ml of aqueous saturated sodium acid sulfite was then slowly added to the stirred mixture. During the addition of the sodium acid sulfite solution, small amounts (about 20 g) of ice were periodically added. The mixture was then stirred for another 15 minutes and extracted with ethyl ether. The ethyl ether extracts were combined, dried over magnesium sulfate and evaporated under vacuum affording 18.4 g of the title compound.

Workup

  1. additionwere periodically added
  2. extractionextracted with ethyl ether
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-dc8afed6f1e6470da0a6400d0a8f8159
Source dataset
uspto-grants-1985_08
Patent number
US04537623

Linked notes

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