Sodium hydride → HCID 57000686, compound

HRID 1609414Notes

Reaction equation

HRID 1609414 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 2.50g of 4-(4'-cyanophenyl)phenol in 5 ml of dimethylformamide 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 dimethylformamide 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-b926428495dd4149b415ad45400a4bc5
Source dataset
uspto-grants-1995_03
Patent number
US05401436

Reaction notes

Loading…