Potassium Cyanide → HCID 18787371, compound

HRID 1602434Notes

Reaction equation

HRID 1602434 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=O)=O.[C-:28]#[N:29].[K+]>CN(C=O)C.O>[C:28]([CH2:6][CH2:7][CH2:8][C:9]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:29]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 18787488HCID 18787488, compound

Product 1

HCID 18787371HCID 18787371, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 2-(3-methanesulfonyloxypropyl)-3-benzyloxybenzoate (19.42 g, 31.7 mmol) and potassium cyanide (2.28 g, 35 mmol) in DMF (50 ml) was heated at 100° C. for 8 hr. The mixture was cooled, diluted with water (250 ml), and extracted three times with ethyl acetate. The ethyl acetate extracts were dried with brine, and concentrated in vacuo. The crude product was chromatographed on silica gel using methylene chloride as the eluent to give the product as an oil (5.25 g, 53%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe ethyl acetate extracts were dried with brine
  4. concentrationconcentrated in vacuo
  5. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-7d92df01e1444f629dec6d1ae6b50015
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

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