Potassium Cyanide → HCID 67422249, compound

HRID 1171842Notes

Reaction equation

HRID 1171842 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([O:9][CH2:10][C:11]2([CH2:14]Br)[CH2:13][CH2:12]2)=[O:8])=[CH:5][CH:4]=1.[C-:18]#[N:19].[K+].C(=O)(O)[O-].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([O:9][CH2:10][C:11]2([CH2:14][C:18]#[N:19])[CH2:13][CH2:12]2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 68535061[1-(Bromomethyl)cyclopropyl]methyl 4-methoxybenzoate

Product 1

HCID 67422249HCID 67422249, compoundYield 17.8%

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-3effd8d3f79f49db9f35a92767ddf711
Source dataset
uspto-grants-2010_11
Patent number
US07829716B2

Reaction notes

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