Potassium Iodide → HCID 54076244, compound

HRID 484167Notes

Reaction equation

HRID 484167 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[I-].[K+].Cl[CH2:26][CH2:27][CH2:28][C:29]#[CH:30]>CS(C)=O>[F:7][C:8]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:9]=1[O:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:30][CH2:29][CH2:28][C:27]#[CH:26])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 843081-Pentyne, 5-chloro-HCID 19750944HCID 19750944, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54076244HCID 54076244, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

With cooling, a solution of 4.2 g of potassium tert-butoxide in 20 ml of anhydrous dimethyl sulfoxide is added to a solution of a 8 g of 4-(2,4-difluorophenoxy)phenol in 20 ml of anhydrous dimethyl sulfoxide and 0.3 g of finely powdered potassium iodide. With stirring, a solution of 4,4 g of 1-chloro-4-pentine in 5 ml of dimethyl sulfoxide is added dropwise at 10°-15° C. to the above mixture. After 2 hours the reaction mixture is warmed to room temperature (20°-23° C.) and stirred for 24 hours at this temperature. The reaction mixture is then poured into ice-water and extracted repeatedly with a 1:2 mixture of diethyl ether/hexane. The combined organic phases are washed until neutral with cold 10% aqueous sodium hydroxide and then with water and dried over sodium sulfate. The solvent is removed by vacuum distillation and the residue is further purified by chromatography over silica gel 60 (eluant: 1:9 mixture of diethyl ether/n-hexane), affording the pure 1-[4-(2,4-difluorophenoxy)phenoxy]-4-pentine with a refractive index nD22 =1.5392.

Workup

  1. temperatureWith cooling
  2. stirringstirred for 24 hours at this temperature
  3. extractionextracted repeatedly with a 1:2 mixture of diethyl ether/hexane
  4. washThe combined organic phases are washed until neutral with cold 10% aqueous sodium hydroxide
  5. dry with materialwith water and dried over sodium sulfate
  6. customThe solvent is removed by vacuum distillation
  7. customthe residue is further purified by chromatography over silica gel 60 (eluant: 1:9 mixture of diethyl ether/n-hexane)

Sources & evidence

ORD record
ord-a01b5fd5634e4fccb30e2e097510dd39
Source dataset
uspto-grants-1993_07
Patent number
US05229426

Reaction notes

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