Sodium hydride → HCID 57000686, compound

HRID 1589759Notes

Reaction equation

HRID 1589759 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)#[N:4].CC1C=CC(S([O-])(=O)=O)=CC=1.[CH3:29][C@@H:30](O)[CH2:31][C@H:32]([OH:34])[CH3:33]>CN(C)C=O>[OH:34][C@@H:32]([CH3:33])[CH2:31][C@@H:30]([CH3:29])[O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:10][CH:9]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 85570p-ToluenesulfonateHCID 1406104'-Hydroxy-4-biphenylcarbonitrileHCID 27236832,4-Pentanediol, (-)-

Product 1

HCID 57000686HCID 57000686, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

0.68 g of 55% sodium hydride was mixed with 10 ml of dimethylformamide. A solution of 2.50 g of 4-(4'-cyanophenyl)phenol in 5 ml of dimethylforamide was added dropwise thereto under ice-cooling. Then the obtained mixture was stirred at room temperature for one hour. A solution of 3.7 g of monotosylate of (R,R)-2,4-pentanediol in 5 ml of dimethylforamide was added dropwise thereto and the obtained mixture was stirred at 80° C. for two hours. After cooling, the reaction mixture was poured into 100 ml of ice-water and extracted with diethyl ether. After washing with water, drying and desolvating, the obtained residue was purified by silica gel column chromatography with the use of a mixture of n-hexane and ethyl acetate (3:2) as a developing solvent. Thus 1.8 g of (R,S)-4-[4'-(3"-hydroxy-1"-methylbutoxy)phenyl]benzonitrile was obtained.

Workup

  1. temperatureunder ice-cooling
  2. stirringthe obtained mixture was stirred at 80° C. for two hours
  3. temperatureAfter cooling
  4. extractionextracted with diethyl ether
  5. washAfter washing with water
  6. customdrying
  7. customthe obtained residue was purified by silica gel column chromatography with the use of a mixture of n-hexane and ethyl acetate (3:2) as a developing solvent

Sources & evidence

ORD record
ord-a87f139008dd4a8fae1839164b3076a4
Source dataset
uspto-grants-1993_04
Patent number
US05200111

Reaction notes

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