Dimethyl Sulfoxide → HCID 22404751, compound

HRID 440693Notes

Reaction equation

HRID 440693 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].[CH3:11][C:12]([OH:16])([C:14]#[CH:15])[CH3:13].CS(C)=O.[OH-].[K+]>>[C:4]([C:3]1[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:2]=1[O:16][C:12]([CH3:13])([CH3:11])[C:14]#[CH:15])#[N:5]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 82582-Methyl-3-butyn-2-olHCID 14797Potassium HydroxideHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 22404751HCID 22404751, compoundYield 47.5%

Procedure

To a stirred solution of 108.3 grams (0.78 mole) of 2,6-difluorobenzonitrile and 78.2 grams (0.93 mole) of 2-methyl-3-butyn-2-ol in 800 mL of dimethyl sulfoxide 65.5 grams (1.17 moles) of potassium hydroxide was added portionwise during a 20 minute period. Upon completion of the addition, the reaction mixture was stirred at ambient temperature for about 18 hours, after which the reaction mixture was poured into ice-water and extracted with diethyl ether. The extract was washed with water and dried with magnesium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure, yielding 75.3 grams of 3-(2-cyano-3-fluoro-phenoxy)-3-methyl-1-butyne. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8301a9f2a44f4b59a501f44eaa71c844
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

Loading…