Acetic Acid → HCID 13854064, compound

HRID 1186535Notes

Reaction equation

HRID 1186535 reaction equation
[C-:1]#[N:2].[K+].[S:4]1[CH:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5]1.C(O)(=O)C.C([O-])(O)=O.[Na+]>CO>[OH:10][CH:9]([C:6]1[CH:7]=[CH:8][S:4][CH:5]=1)[C:1]#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 681353-ThiophenecarboxaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 13854064HCID 13854064, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

To a stirred suspension of KCN (18.6 g, 286 mmol) in methanol (100 mL) was added thiophene-3-carbaldehyde (20 mL, 178 mmol) at 0° C. under nitrogen atmosphere. Then acetic acid (4.4 mL) was added dropwise at 0° C. After 30 minutes, the mixture was warmed to 15° C. and stirred for 20 hours. NaHCO3 (15 g) was added. The mixture was concentrated and extracted with ethyl acetate (200 mL). The organic mixture was washed with water (3×25 mL), brine (25 mL), dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by column chromatography (ethyl acetate:petroleum ether, 1:10) to afford hydroxy-thiophen-3-yl-acetonitrile. (Yield 15 g, 60%). LC-MS: [M+Na]+ 162.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with ethyl acetate (200 mL)
  3. washThe organic mixture was washed with water (3×25 mL), brine (25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography (ethyl acetate:petroleum ether, 1:10)

Sources & evidence

ORD record
ord-83089c9c1884487983c979936eb95471
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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