Potassium Cyanide → HCID 14293633, compound

HRID 388266Notes

Reaction equation

HRID 388266 reaction equation
[S:1]1[C:5]([CH:6]=[O:7])=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.OS([O-])=O.[Na+].[C-:17]#[N:18].[K+]>C1COCC1.O.[Cl-].[Na+].O>[S:1]1[C:5]([CH:6]([OH:7])[C:17]#[N:18])=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2

Participants

7

Reactant 3

HCID 9032Potassium CyanideHCID 7365001-Benzothiophene-2-carbaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 14293633HCID 14293633, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of benzo[b]thiophene-2-carbaldehyde (2.19 g, 13.5 mmol) in anhydrous THF (200 mL) was added a solution of NaHSO3 (6.18 g, 59.4 mmol) in water (50 mL). KCN (3.248 g, 49.9 mmol) was added and the mixture was stirred at room temperature for 22 hours. The reaction mixture was then heated at 45° C. for 1 hour. After cooling to room temperature, the mixture was diluted with water and brine and extracted with EtOAc three times. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-25% EtOAc-hexanes) gave 2-(benzo[b]thiophen-2-yl)-2-hydroxyacetonitrile as an off-white solid (1.09 g, 46% yield).

Workup

  1. temperatureThe reaction mixture was then heated at 45° C. for 1 hour
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with EtOAc three times
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography (0-25% EtOAc-hexanes)

Sources & evidence

ORD record
ord-e56f25395c9b4fac9f22eb5e34cf856f
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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