Potassium Cyanide → HCID 67422249, compound

HRID 1784094Notes

Reaction equation

HRID 1784094 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([O:9][CH2:10][CH:11]2[CH2:13][CH:12]2CBr)=[O:8])=[CH:5][CH:4]=1.[C-:18]#[N:19].[K+].[C:21](=O)(O)[O-].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][C:11]2([CH2:21][C:18]#[N:19])[CH2:12][CH2:13]2)=[O:8])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 67424348HCID 67424348, compound

Product 1

HCID 67422249HCID 67422249, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

261 mg of compound 10a was dissolved in 5 ml ethanol. A solution of 98 mg potassium cyanide in 5 ml water was added and the mixture was stirred at 35° C. for two days. 10 ml of a saturated aqueous sodium bicarbonate was added. The mixture was extracted twice with ethyl acetate. The combined extracts were dried with sodium sulfate and evaporated to give a yellow liquid. Purification with column chromatography (heptane/ethyl acetate 3/1) gave the title compound (38 mg) confirmed by NMR and LC/MS

Workup

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. dry with materialThe combined extracts were dried with sodium sulfate
  3. customevaporated
  4. customto give a yellow liquid
  5. customPurification with column chromatography (heptane/ethyl acetate 3/1)

Sources & evidence

ORD record
ord-0acb0b6fd4e84fcfbd9ddc5057e095ed
Source dataset
uspto-grants-2009_03
Patent number
US07501517B2

Reaction notes

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